N-(tetrazol-5-yl)- and n-(triazol-5-yl)arylcarboxylic thioamides and use thereof as herbicides

ABSTRACT

N-(Tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxylic acid thioamides of the general formula (I) are described as herbicides. 
     
       
         
         
             
             
         
       
     
     In this formula (I), R, W, X and Z represent radicals such as hydrogen, organic radicals such as alkyl, and other radicals such as halogen. A and B each represent carbon or nitrogen.

The invention relates to the technical field of herbicides, especiallythat of herbicides for the selective control of broad-leaved weeds andweed grasses in crops of useful plants.

WO 2012/028579 A1 discloses N-(tetrazol-5-yl)- andN-(triazol-5-yl)nicotinamides as herbicides. However, these activecompounds are not always sufficiently active against harmful plantsand/or some of them are not sufficiently compatible with some importantcrop plants such as cereal species, corn or rice.

Accordingly, it is an object of the present invention to provide furtherherbicidally active compounds. This object is achieved by theN-(tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxylic acid thioamidesaccording to the invention described below which, owing to the thioamidestructure, differ substantially from the compounds known from the priorart.

The present invention thus provides N-(tetrazol-5-yl)- andN-(triazol-5-yl)arylcarboxylic acid thioamides of the formula (I) orsalts thereof

in which

A represents N or CY,

B represents N or CH,

X represents nitro, halogen, cyano, formyl, thiocyanato, (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, halo-(C₃-C₆)-alkynyl, (C₃-C₆)-cycloalkyl,halo-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, COR¹, COOR¹, OCOOR¹, NR¹COOR¹,C(O)N(R¹)₂, NR¹C(O)N(R¹)₂, OC(O)N(R¹)₂, C(O)NR¹OR¹, OR¹, OCOR¹, OSO₂R²,S(O)_(n)R², SO₂OR¹, SO₂N(R¹)₂, NR¹SO₂R², NR¹COR¹,(C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-OCOR¹,(C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-CO₂R¹, (C₁-C₆)-alkyl-SO₂OR¹,(C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹,(C₁-C₆)-alkyl-NR¹SO₂R², NR₁R₂, P(O)(OR⁵)₂, CH₂P(O)(OR⁵)₂,(C₁-C₆)-alkylheteroaryl or (C₁-C₆)-alkylheterocyclyl, where the twolast-mentioned radicals are each substituted by s radicals from thegroup consisting of halogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy and halo-(C₁-C₆)-alkoxy, andwhere heterocyclyl carries n oxo groups,

Y represents hydrogen, nitro, halogen, cyano, thiocyanato,(C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, halo-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,COR¹, COOR¹, OCOOR¹, NR¹COOR¹, C(O)N(R¹)₂, NR¹C(O)N(R¹)₂, OC(O)N(R¹)₂,CO(NOR¹)R¹, CHNOR¹, CH₂ONC(R³)₂, NR¹SO₂R², NR¹COR¹, OR¹, OSO₂R²,S(O)_(n)R², SO₂OR¹, SO₂N(R¹)₂ (C₁-C₆)-alkyl-S(O)_(n)R², NS(O)R⁸R⁷,S(O)R⁸NR⁹, (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-OSO₂R²,(C₁-C₆)-alkyl-CO₂R¹, (C₁-C₆)-alkyl-CN, (C₁-C₆)-alkyl-SO₂OR¹,(C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹,(C₁-C₆)-alkyl-NR¹SO₂R², N(R¹)₂, P(O)(OR⁵)₂, CH₂P(O)(OR⁵)₂,(C₁-C₆)-alkylphenyl, (C₁-C₆)-alkylheteroaryl, (C₁-C₆)-alkylheterocyclyl,phenyl, heteroaryl or heterocyclyl, where the six last-mentionedradicals are each substituted by s radicals from the group consisting ofhalogen, nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy,halo-(C₁-C₆)-alkoxy, (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl and cyanomethyl, andwhere heterocyclyl carries n oxo groups,

Z represents halogen, cyano, nitro, thiocyanato, halo-(C₁-C₆)-alkyl,(C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,halo-(C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,COR¹, COOR¹, OCOOR¹, NR¹COOR¹, C(O)N(R¹)₂, NR¹C(O)N(R¹)₂, OC(O)N(R¹)₂,C(O)NR¹OR¹, OSO₂R², S(O)_(n)R², SO₂OR¹, SO₂N(R¹)₂, NR¹SO₂R², NR¹COR¹,(C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-OCOR¹,(C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-CO₂R¹, (C₁-C₆)-alkyl-SO₂OR¹,(C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹,(C₁-C₆)-alkyl-NR¹SO₂R², N(R¹)₂, P(O)(OR⁵)₂, heteroaryl, heterocyclyl orphenyl, where the three last-mentioned radicals are each substituted bys radicals from the group consisting of halogen, nitro, cyano,(C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy and halo-(C₁-C₆)-alkoxy, andwhere heterocyclyl carries n oxo groups,

or

Z may also represent hydrogen, (C₁-C₆)-alkyl or (C₁-C₆)-alkoxy if Yrepresents the S(O)_(n)R² radical,

W represents hydrogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,halo-(C₂-C₆)-alkynyl, (C₃-C₇)-cycloalkyl, (C₃-C₇)-halocycloalkyl,(C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy, S(O)_(n)—(C₁-C₆)-alkyl,S(O)_(n)—(C₁-C₆)-haloalkyl, (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl,(C₁-C₆)-alkoxy-(C₁-C₄)-haloalkyl, halogen, nitro, NR³COR³ or cyano,

R represents (C₁-C₈)-alkyl, halo-(C₁-C₈)-alkyl, (C₂-C₈)-alkenyl,halo-(C₂-C₈)-alkenyl, (C₂-C₈)-alkynyl or halo-(C₂-C₈)-alkynyl, wherethese six abovementioned radicals are each substituted by s radicalsfrom the group consisting of hydroxy, nitro, cyano, SiR⁵ ₃, PO(OR⁵)₂,S(O)_(n)—(C₁-C₆)-alkyl, S(O)_(n)—(C₁-C₆)-haloalkyl, (C₁-C₆)-alkoxy,halo-(C₁-C₆)-alkoxy, N(R³)₂, COR³, COOR³, OCOR³, NR³COR³, NR³SO₂R⁴,O(C₁-C₂)-alkyl-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl, heteroaryl,heterocyclyl, phenyl, Q-heteroaryl, Q-heterocyclyl, Q-phenyl andQ-benzyl, where the seven last-mentioned radicals are each substitutedby s radicals from the group consisting of methyl, ethyl, methoxy,trifluoromethyl, cyano and halogen, and where heterocyclyl carries n oxogroups, or

R represents (C₃-C₇)-cycloalkyl, heteroaryl, heterocyclyl or phenyl,each of which is substituted by s radicals from the group consisting ofhalogen, nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy,halo-(C₁-C₆)-alkoxy and (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, where heterocyclylcarries n oxo groups,

Q represents 0, S or NR³,

R¹ represents hydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl,(C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl,(C₂-C₆)-haloalkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl,(C₃-C₆)-halocycloalkyl, (C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl, phenyl-(C₁-C₆)-alkyl,heteroaryl, (C₁-C₆)-alkyl-heteroaryl, heterocycle,(C₁-C₆)-alkyl-heterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,(C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR³-heteroaryl or(C₁-C₆)-alkyl-NR³-heterocyclyl, where the 21 last-mentioned radicals areeach substituted by s radicals from the group consisting of cyano,halogen, nitro, thiocyanato, OR³, S(O)_(n)R⁴, N(R³)₂, NR³OR³, COR³,OCOR³, SCOR⁴, NR³COR³, NR³SO₂R⁴, CO₂R³, COSR⁴, CON(R³)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl carries noxo groups,

R² represents (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, (C₃-C₆)-halocycloalkyl,(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl,phenyl-(C₁-C₆)-alkyl, heteroaryl, (C₁-C₆)-alkylheteroaryl, heterocyclyl,(C₁-C₆)-alkylheterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,(C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR³-heteroaryl or(C₁-C₆)-alkyl-NR³-heterocyclyl, where the 21 last-mentioned radicals areeach substituted by s radicals from the group consisting of cyano,halogen, nitro, thiocyanato, OR³, S(O)_(n)R⁴, N(R³)₂, NR³OR³, COR³,OCOR³, SCOR⁴, NR³COR³, NR³SO₂R⁴, CO₂R³, COSR⁴, CON(R³)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl carries noxo groups,

R³ represents hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl or phenyl,

R⁴ represents (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl or phenyl,

R⁵ represents (C₁-C₄)-alkyl,

R⁶ and R⁷ each independently of one another represent (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, halo-(C₃-C₆)-alkynyl, (C₃-C₆)-cycloalkyl,halo-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl,halo-(C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, phenyl, heteroaryl or heterocyclyl,where the three last-mentioned radicals are each substituted by sradicals from the group consisting of nitro, halogen, cyano,thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,R¹O(O)C, (R¹)₂N(O)C, R¹O, (R¹)₂N, R²(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S andR¹O—(C₁-C₆)-alkyl, and where heterocyclyl carries n oxo groups, or

R⁶ and R⁷ together with the sulfur atom to which they are bonded form a3- to 8-membered unsaturated, semisaturated or saturated ring whichcontains, apart from the carbon atoms and apart from the sulfur atom ofthe sulfoximino group, in each case m ring members from the groupconsisting of N(R¹), O and S(O)_(n), and where this ring in each case issubstituted by s radicals from the group consisting of nitro, halogen,cyano, thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, R¹O(O)C, (R¹)₂N(O)C, R¹O, (R¹)₂N, R²(O)_(n)S,R¹O(O)₂S, (R¹)₂N(O)₂S and R¹O—(C₁-C₆)-alkyl, and where this ring bears noxo groups,

R⁸ represents (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl, each ofwhich is substituted by s radicals from the group consisting of nitro,halogen, cyano, thiocyanato, (C₃-C₆)-cycloalkyl, R¹(O)C, R¹(R¹ON═)C,R¹O(O)C, (R¹)₂N(O)C, R¹(R¹O)N(O)C, R²(O)₂S(R¹)N(O)C, R¹O(O)₂S(R¹)N(O)C,(R¹)₂N(O)₂S(R¹)N(O)C, R¹S(O)C, R¹O, R¹(O)CO, R²(O)₂SO, R²O(O)CO,(R¹)₂N(O)CO, (R¹)₂N, R¹O(R¹)N, R¹(O)C(R¹)N, R²(O)₂S(R¹)N, R²O(O)C(R¹)N,(R¹)₂N(O)C(R¹)N, R¹O(O)₂S(R¹)N, (R¹)₂N(O)₂S(R¹)N, R²(O)_(n)S, R¹C(O)S,R¹O(O)₂S, (R¹)₂N(O)₂S, R¹(O)C(R¹)N(O)₂S, R²O(O)C(R¹)N(O)₂S,(R¹)₂N(O)C(R¹)N(O)₂S and (R⁶O)₂(O)P,

or

(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, phenyl, phenyl-(C₁-C₆)-alkyl,heteroaryl, heteroaryl-(C₁-C₆)-alkyl, heterocyclyl,heterocyclyl-(C₁-C₆)-alkyl, phenyl-O—(C₁-C₆)-alkyl,heteroaryl-O—(C₁-C₆)-alkyl, heterocyclyl-O—(C₁-C₆)-alkyl,phenyl-N(R¹)—(C₁-C₆)-alkyl, heteroaryl-N(R¹)—(C₁-C₆)-alkyl,heterocyclyl-N(R¹)—(C₁-C₆)-alkyl, phenyl-S(O)_(n)—(C₁-C₆)-alkyl,heteroaryl-S(O)_(n)—(C₁-C₆)-alkyl orheterocyclyl-S(O)_(n)—(C₁-C₆)-alkyl, each of which is substituted in thecyclic moiety by s radicals from the group consisting of nitro, halogen,cyano, thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, R¹(O)C, R¹(R¹ON═)C, R¹O(O)C, (R¹)₂N(O)C,R¹(R¹O)N(O)C, R²(O)₂S(R¹)N(O)C, R¹O(O)₂S(R¹)N(O)C, (R¹)₂N(O)₂S(R¹)N(O)C,R¹S(O)C, R¹O, R¹(O)CO, R₂(O)₂SO, R²O(O)CO, (R¹)₂N(O)CO, (R¹)₂N,R¹O(R¹)N, R¹(O)C(R¹)N, R²(O)₂S(R¹)N, R²O(O)C(R¹)N, (R¹)₂N(O)C(R¹)N,R¹O(O)₂S(R¹)N, (R¹)₂N(O)₂S(R¹)N, R²(O)_(n)S, R¹C(O)S, R¹O(O)₂S,(R¹)₂N(O)₂S, R¹(O)C(R¹)N(O)₂S, R²O(O)C(R¹)N(O)₂S, (R¹)₂N(O)C(R¹)N(O)₂S,(R⁵O)₂(O)P and R¹O—(C₁-C₆)-alkyl, and where heterocyclyl carries n oxogroups,

R⁹ represents hydrogen, nitro, halogen, cyano, (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, (C₃-C₆)-alkenyl, halo-(C₃-C₆)-alkenyl,(C₂-C₆)-alkynyl, halo-(C₃-C₆)-alkynyl, (C₃-C₆)-Cycloalkyl,halo-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, R¹(O)C, R²O(O)C, (R¹)₂N(O)C,R²S(O)C, (R¹)₂N(S)C, R¹(R¹O)N(O)C, R²(O)₂S(R¹)N(O)C,(R¹)₂N(O)₂S(R¹)N(O)C, R¹O, (R¹)₂N, R²(O)_(n)S,(R²)₃Si—(C₁-C₆)-alkyl-(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S, R¹(O)C(R¹)N(O)₂S,R²O(O)C(R¹)N(O)₂S, (R¹)₂N(O)C(R¹)N(O)₂S, R²(O)₂S(R¹)N(O)₂S, (R⁵O)₂(O)P,(R²)₃Si, R¹(O)C—(C₁-C₆)-alkyl, R¹O(O)C—(C₁-C₆)-alkyl,(R¹)₂N(O)C—(C₁-C₆)-alkyl, (R¹O)(R¹)N(O)C—(C₁-C₆)-alkyl,R²(O)₂S(R¹)N(O)C—(C₁-C₆)-alkyl, R¹O(O)₂S(R¹)N(O)C—(C₁-C₆)-alkyl,(R¹)₂N(O)₂S(R¹)N(O)C—(C₁-C₆)-alkyl, R¹O—(C₁-C₆)-alkyl,R¹(O)CO—(C₁-C₆)-alkyl, R²(O)₂SP—(C₁-C₆)-alkyl, R²O(O)CO—(C₁-C₆)-alkyl,(R¹)₂N(O)CO—(C₁-C₆)-alkyl, (R¹)₂N—(C₁-C₆)-alkyl,R¹(O)C(R¹)N—(C₁-C₆)-alkyl, R²(O)₂S(R¹)N—(C₁-C₆)-alkyl,R²O(O)C(R¹)N—(C₁-C₆)-alkyl, (R¹)₂N(O)C(R¹)N—(C₁-C₆)-alkyl,R¹O(O)₂S(R¹)N—(C₁-C₆)-alkyl, (R¹)₂N(O)₂S(R¹)N—(C₁-C₆)-alkyl,R²(O)_(n)S—(C₁-C₆)-alkyl, R¹O(O)₂S—(C₁-C₆)-alkyl,(R¹)₂N(O)₂S—(C₁-C₆)-alkyl, R¹(O)C(R¹)N(O)₂S—(C₁-C₆)-alkyl,R²O(O)C(R¹)N(O)₂S—(C₁-C₆)-alkyl, (R¹)₂N(O)C(R¹)N(O)₂S—(C₁-C₆)-alkyl,(R⁵O)₂(O)P—(C₁-C₆)-alkyl, (R²)₃Si—(C₁-C₆)-alkyl,

or

phenyl, heteroaryl, heterocyclyl, phenyl-(C₁-C₆)-alkyl,heteroaryl-(C₁-C₆)-alkyl or heterocyclyl-(C₁-C₆)-alkyl, each of which issubstituted in the cyclic moiety by s radicals from the group consistingof nitro, halogen, cyano, thiocyanato, (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, R¹O(O)C, (R¹)₂N(O)C, R¹O,(R¹)₂N, R²(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S and R¹O—(C₁-C₆)-alkyl, andwhere heterocyclyl carries n oxo groups,

m represents 0, 1, 2, 3 or 4,

n represents 0, 1 or 2,

s represents 0, 1, 2 or 3.

In the formula (I) and all the formulae which follow, alkyl radicalshaving more than two carbon atoms may be straight-chain or branched.Alkyl radicals represent, for example, methyl, ethyl, n- or isopropyl,n-, iso-, tert- or 2-butyl, pentyls, hexyls such as n-hexyl, isohexyland 1,3-dimethylbutyl. Analogously, alkenyl represents, for example,allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl,but-3-en-1-yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl. Alkynylrepresents, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl,1-methylbut-3-yn-1-yl. The multiple bond may be in each case in anyposition of the unsaturated radical. Cycloalkyl represents a carbocyclicsaturated ring system having three to six carbon atoms, for examplecyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Analogously,cycloalkenyl represents a monocyclic alkenyl group having three to sixcarbon ring members, for example cyclopropenyl, cyclobutenyl,cyclopentenyl and cyclohexenyl, where the double bond may be in anyposition.

Halogen represents fluorine, chlorine, bromine or iodine.

Heterocyclyl represents a saturated, semisaturated or fully unsaturatedcyclic radical containing 3 to 6 ring atoms, of which 1 to 4 are fromthe group consisting of oxygen, nitrogen and sulfur, and which mayadditionally be fused by a benzo ring. For example, heterocyclylrepresents piperidinyl, pyrrolidinyl, tetrahydrofuranyl, dihydrofuranyland oxetanyl.

Heteroaryl represents an aromatic cyclic radical containing 3 to 6 ringatoms, of which 1 to 4 are from the group consisting of oxygen, nitrogenand sulfur, and which may additionally be fused by a benzo ring. Forexample, heteroaryl represents benzimidazol-2-yl, furanyl, imidazolyl,isoxazolyl, isothiazolyl, oxazolyl, pyrazinyl, pyrimidinyl, pyridazinyl,pyridinyl, benzisoxazolyl, thiazolyl, pyrrolyl, pyrazolyl, thiophenyl,1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl,1,3,4-oxadiazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,2,5-triazolyl,1,3,4-triazolyl, 1,2,4-triazolyl, 1,2,4-thiadiazolyl,1,3,4-thiadiazolyl, 1,2,3-thiadiazolyl, 1,2,5-thiadiazolyl,2H-1,2,3,4-tetrazolyl, 1H-1,2,3,4-tetrazolyl, 1,2,3,4-oxatriazolyl,1,2,3,5-oxatriazolyl, 1,2,3,4-thiatriazolyl and 1,2,3,5-thiatriazolyl.

When a group is polysubstituted by radicals, this means that this groupis substituted by one or more identical or different radicals from thosementioned. This applies analogously to the formation of ring systems byvarious atoms and elements. At the same time, the scope of the claimsshall exclude those compounds known to the person skilled in the art tobe chemically unstable under standard conditions.

Depending on the nature of the substituents and manner in which they areattached, the compounds of the general formula (I) may be present asstereoisomers. If, for example, one or more asymmetric carbon atoms arepresent, there may be enantiomers and diastereomers. Stereoisomerslikewise occur when n represents 1 (sulfoxides). Stereoisomers can beobtained from the mixtures obtained in the preparation by customaryseparation methods, for example by chromatographic separation processes.It is likewise possible to selectively prepare stereoisomers by usingstereoselective reactions with use of optically active startingmaterials and/or auxiliaries. The invention also relates to allstereoisomers and mixtures thereof which are encompassed by the generalformula (I) but not defined specifically.

The compounds of the formula (I) may form salts. Salts may be formed byaction of a base on compounds of the formula (I). Examples of suitablebases are organic amines such as trialkylamines, morpholine, piperidineand pyridine, and the hydroxides, carbonates and hydrogencarbonates ofammonium, alkali metals or alkaline earth metals, in particular sodiumhydroxide, potassium hydroxide, sodium carbonate, potassium carbonate,sodium hydrogencarbonate and potassium hydrogencarbonate. These saltsare compounds in which the acidic hydrogen is replaced by anagriculturally suitable cation, for example metal salts, in particularalkali metal salts or alkaline earth metal salts, in particular sodiumand potassium salts, or else ammonium salts, salts with organic aminesor quaternary ammonium salts, for example with cations of the formula[NR^(a)R^(b)R^(c)R^(d)]⁺, in which R^(a) to R^(d) in each caseindependently of one another represent an organic radical, in particularalkyl, aryl, aralkyl or alkylaryl. Also useful are alkylsulfonium andalkylsulfoxonium salts, such as (C₁-C₄)-trialkylsulfonium and(C₁-C₄)-trialkylsulfoxonium salts.

The compounds of the formula (I) can form salts by addition of asuitable inorganic or organic acid, for example mineral acids, forexample HCl, HBr, H₂SO₄, H₃PO₄ or HNO₃, or organic acids, for examplecarboxylic acids such as formic acid, acetic acid, propionic acid,oxalic acid, lactic acid or salicylic acid, or sulfonic acids, forexample p-toluenesulfonic acid, onto a basic group, for example amino,alkylamino, dialkylamino, piperidino, morpholino or pyridino.

Preference is given to compounds of the general formula (I) in which

A represents N or CY,

B represents N or CH,

X represents nitro, halogen, cyano, thiocyanato, (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, halo-(C₃-C₆)-alkynyl, (C₃-C₆)-cycloalkyl,halo-(C₃-C₆)-cycloalkyl, (C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,COR¹, OR¹, OCOR¹, OSO₂R², S(O)_(n)R², SO₂OR¹, SO₂N(R¹)₂, NR¹SO₂R²,NR¹COR¹, (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹,(C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-CO₂R¹,(C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂,(C₁-C₆)-alkyl-NR¹COR¹ or (C₁-C₆)-alkyl-NR¹SO₂R²,(C₁-C₆)-alkyl-heteroaryl or (C₁-C₆)-alkyl-heterocyclyl, where the twolast-mentioned radicals are each substituted by s radicals from thegroup consisting of halogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy and halo-(C₁-C₆)-alkoxy, andwhere heterocyclyl carries n oxo groups,

Y represents hydrogen, nitro, halogen, cyano, thiocyanato,(C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₃-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, halo-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,COR¹, OR¹, COOR¹, CHNOR¹, CH₂ONC(R³)₂, OSO₂R², S(O)_(n)R², SO₂OR¹,SO₂N(R¹)₂, NS(O)R⁶R⁷, S(O)R⁸NR⁹, N(R¹)₂, NR¹SO₂R², NR¹COR¹,(C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-OCOR¹,(C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-CO₂R¹, (C₁-C₆)-alkyl-SO₂OR¹,(C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹,(C₁-C₆)-alkyl-NR¹SO₂R², (C₁-C₆)-alkyl-phenyl, (C₁-C₆)-alkyl-heteroaryl,(C₁-C₆)-alkyl-heterocyclyl, phenyl, heteroaryl or heterocyclyl, wherethe six last-mentioned radicals are each substituted by s radicals fromthe group consisting of halogen, nitro, cyano, (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, S(O)_(n)—(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy, (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl andcyanomethyl, and where heterocyclyl carries n oxo groups,

Z represents halogen, cyano, nitro, thiocyanato, halo-(C₁-C₆)-alkyl,(C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,halo-(C₃-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,COR¹, COOR¹, C(O)N(R¹)₂, C(O)NR¹OR¹, OSO₂R², S(O)_(n)R², SO₂OR¹,SO₂N(R¹)₂, NR¹SO₂R², NR¹COR¹, (C₁-C₆)-alkyl-S(O)_(n)R²,(C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-OSO₂R²,(C₁-C₆)-alkyl-CO₂R¹, (C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂,(C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R²or 1,2,4-triazol-1-yl,

or

Z may also represent hydrogen, (C₁-C₆)-alkyl or (C₁-C₆)-alkoxy if Yrepresents the S(O)_(n)R² radical,

W represents hydrogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy, S(O)_(n)—(C₁-C₆)-alkyl,S(O)_(n)—(C₁-C₆)-haloalkyl, (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, halogen, nitroor cyano,

R represents (C₁-C₆-alkyl, halo-(C₁-C₆-alkyl, (C₂-C₆)-alkenyl,halo-(C₂-C₈)-alkenyl, (C₂-C₈)-alkynyl, halo-(C₂-C₈)-alkynyl, where thesesix abovementioned radicals are each substituted by s radicals from thegroup consisting of nitro, cyano, SiR⁵ ₃, P(OR⁵)₃,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy, N(R³)₂,COR³, COOR³, OCOR³, NR³COR³, NR³SO₂R⁴, (C₃-C₆)-cycloalkyl, heteroaryl,heterocyclyl, phenyl, Q-heteroaryl, Q-heterocyclyl, Q-phenyl andQ-benzyl, where the seven last-mentioned radicals are each substitutedby s radicals from the group consisting of methyl, ethyl, methoxy,trifluoromethyl, cyano and halogen, and where heterocyclyl carries n oxogroups, or

R represents (C₃-C₇)-cycloalkyl, heteroaryl, heterocyclyl or phenyl,each of which is substituted by s radicals from the group consisting ofhalogen, nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy,halo-(C₁-C₆)-alkoxy and (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl,

Q represents O, S or NR³,

R¹ represents hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, phenyl, phenyl-(C₁-C₆)-alkyl, heteroaryl,(C₁-C₆)-alkylheteroaryl, heterocyclyl, (C₁-C₆)-alkylheterocyclyl,(C₁-C₆)-alkyl-O-heteroaryl, (C₁-C₆)-alkyl-O-heterocyclyl,(C₁-C₆)-alkyl-NR³-heteroaryl or (C₁-C₆)-alkyl-NR³-heterocyclyl, wherethe sixteen last-mentioned radicals are each substituted by s radicalsfrom the group consisting of cyano, halogen, nitro, OR³, S(O)_(n)R⁴,N(R³)₂, NR³OR³, COR³, OCOR³, NR³COR³, NR³SO₂R⁴, CO₂R³, CON(R³)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl carries noxo groups,

R² represents (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, phenyl, phenyl-(C₁-C₆)-alkyl, heteroaryl,(C₁-C₆)-alkylheteroaryl, heterocyclyl, (C₁-C₆)-alkylheterocyclyl,(C₁-C₆)-alkyl-O-heteroaryl, (C₁-C₆)-alkyl-O-heterocyclyl,(C₁-C₆)-alkyl-NR³-heteroaryl or (C₁-C₆)-alkyl-NR³-heterocyclyl, wherethese sixteen last-mentioned radicals are each substituted by s radicalsfrom the group consisting of cyano, halogen, nitro, OR³, S(O)_(n)R⁴,N(R³)₂, NR³OR³, NR³SO₂R⁴, COR³, OCOR³, NR³COR³, CO₂R³, CON(R³)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl carries noxo groups,

R³ represents hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl or (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,

R⁴ represents (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl,

R⁵ represents methyl or ethyl,

R⁶ and R⁷ each independently of one another represent (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, halo-(C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, phenyl,heteroaryl or heterocyclyl, where the three last-mentioned radicals areeach substituted by s radicals from the group consisting of nitro,halogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, R¹O(O)C, (R¹)₂N(O)C, R¹O,(R¹)₂N, R²(O)_(n)S and R¹O—(C₁-C₆)-alkyl, and where heterocyclyl carriesn oxo groups,

or R⁶ and R⁷ together with the sulfur atom to which they are attachedform a 3- to 8-membered unsaturated, partially saturated or saturatedring which contains, in addition to the carbon atoms and in addition tothe sulfur atom of the sulfoximino group, in each case m ring membersfrom the group consisting of N(R¹), O and S(O)_(n), and where this ringis in each case substituted by s radicals from the group consisting ofhalogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, R¹O(O)C, (R¹)₂N(O)C, R¹O,(R¹)₂N, R²(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S and R¹O—(C₁-C₆)-alkyl, andwhere this ring carries n oxo groups,

R⁸ represents (C₁-C₆)-alkyl which is in each case substituted by sradicals from the group consisting of halogen, cyano,(C₃-C₆)-cycloalkyl, R¹(O)C, R¹(R¹ON═)C, R¹O(O)C, (R¹)₂N(O)C,R²(O)₂S(R¹)N(O)C, R¹O, (R¹)₂N, R¹(O)C(R¹)N, R²(O)₂S(R¹)N, R²O(O)C(R¹)N,(R¹)₂N(O)C(R¹)N, R²(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S, R¹(O)C(R¹)N(O)₂S,R²O(O)C(R¹)N(O)₂S and (R¹)₂N(O)C(R¹)N(O)₂S or (C₃-C₆)-cycloalkyl whichis in each case substituted by s radicals from the group consisting ofhalogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, R¹O(O)Cand (R¹)₂N(O)C,

R⁹ represents hydrogen, nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,R¹(O)C, R²O(O)C, (R¹)₂N(O)C, R²(O)₂S, R¹(O)C—(C₁-C₆)-alkyl,R¹O(O)C—(C₁-C₆)-alkyl, (R¹)₂N(O)C—(C₁-C₆)-alkyl, R¹O—(C₁-C₆)-alkyl,(R¹)₂N—(C₁-C₆)-alkyl or R²(O)_(n)S—(C₁-C₆)-alkyl,

m represents 0, 1 or 2,

n represents 0, 1 or 2,

s represents 0, 1, 2 or 3.

Particular preference is given to compounds of the general formula (I)in which

A represents N or CY,

B represents N or CH,

X represents nitro, halogen, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, OR¹, S(O)_(n)R², (C₁-C₆)-alkyl-S(O)_(n)R²,(C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂,(C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R², (C₁-C₆)-alkylheteroarylor (C₁-C₆)-alkylheterocyclyl, where the two last-mentioned radicals areeach substituted by s halogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy and halo-(C₁-C₆)-alkoxy radicals,and where heterocyclyl carries n oxo groups,

Y hydrogen, nitro, halogen, cyano, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl,OR¹, S(O)_(n)R², SO₂N(R¹)₂, NS(O)R⁶R⁷, S(O)R⁸NR⁹, N(R¹)₂, CHNOR¹,CH₂ONC(R³)₂, NR¹SO₂R², NR¹COR¹, (C₁-C₆)-alkyl-S(O)_(n)R²,(C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂,(C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R², (C₁-C₆)-alkyl-phenyl,(C₁-C₆)-alkyl-heteroaryl, (C₁-C₆)-alkyl-heterocyclyl, phenyl, heteroarylor heterocyclyl, where the six last-mentioned radicals are eachsubstituted by s radicals from the group consisting of halogen, nitro,cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy,(C₁-C₆)-alkoxy-(C₁-C₄)-alkyl and cyanomethyl, and where heterocyclylcarries n oxo groups,

Z represents halogen, cyano, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,S(O)_(n)R², 1,2,4-triazol-1-yl,

or

Z may also represent hydrogen, methyl, methoxy or ethoxy if Y representsthe S(O)_(n)R² radical,

W represents hydrogen, methyl, ethyl, methoxymethyl, methoxy, fluorine,chlorine or S(O)_(n)CH₃,

R represents (C₁-C₈)-alkyl, halo-(C₁-C₈)-alkyl, (C₂-C₈)-alkenyl,halo-(C₂-C₈)-alkenyl, (C₂-C₈)-alkynyl, halo-(C₂-C₈)-alkynyl, where thesesix abovementioned radicals are each substituted by s radicals from thegroup consisting of cyano, S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy,halo-(C₁-C₆)-alkoxy, COR³, COOR³, OCOR³, NR³COR³, NR³SO₂R⁴,(C₃-C₆)-cycloalkyl, heteroaryl, heterocyclyl and phenyl, where the threelast-mentioned radicals are each substituted by s radicals from thegroup consisting of methyl, ethyl, methoxy, trifluoromethyl, cyano andhalogen, and where heterocyclyl carries 0 to 2 oxo groups,

or

R represents phenyl which is substituted by s radicals from the groupconsisting of halogen, nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy,halo-(C₁-C₆)-alkoxy and (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl,

R¹ represents hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, phenyl, phenyl-(C₁-C₆)-alkyl, heteroaryl,(C₁-C₆)-alkylheteroaryl, heterocyclyl, (C₁-C₆)-alkylheterocyclyl,(C₁-C₆)-alkyl-O-heteroaryl, (C₁-C₆)-alkyl-O-heterocyclyl,(C₁-C₆)-alkyl-NR³-heteroaryl or (C₁-C₆)-alkyl-NR³-heterocyclyl, wherethe sixteen last-mentioned radicals are each substituted by s radicalsfrom the group consisting of cyano, halogen, nitro, OR³, S(O)_(n)R⁴,N(R³)₂, NR³OR³, COR³, OCOR³, NR³COR³, NR³SO₂R⁴, CO₂R³, CON(R³)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl carries noxo groups,

R² represents (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl or(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, each substituted by s radicals fromthe group consisting of halogen and OR³,

R³ represents hydrogen or (C₁-C₆)-alkyl,

R⁴ represents (C₁-C₆)-alkyl,

R⁶ and R⁷ independently of one another each represent methyl, ethyl orn-propyl,

or

R⁶ and R⁷ together with the sulfur atom to which they are attached forma 5- or 6-membered saturated ring which, in addition to the carbon atomsand in addition to the sulfur atom of the sulfoximino group, contains moxygen atoms,

R⁸ represents methyl, ethyl or n-propyl,

R⁹ represents hydrogen or cyano,

m represents 0 or 1,

n represents 0, 1 or 2,

s represents 0, 1, 2 or 3.

In all the formulae specified hereinafter, the substituents and symbolshave the same meaning as described in formula (I), unless defineddifferently.

Compounds according to the invention can be prepared, for example, bythe method indicated in Scheme 1 by reacting an N-(tetrazol-5-yl)- andN-(triazol-5-yl)benzamide and nicotinamide (II) with a sulfurizing agentsuch as, for example, phosphorus pentasulfide or Lawesson's reagent:

The N-(tetrazol-5-yl)- and N-(triazol-5-yl)benzamides and nicotinamidesof the formula (II) can be prepared, for example, by the methodsdescribed in WO 2012/028579 A1, EP 11158253 and EP 11159115.

It may be expedient to change the order of reaction steps. Thus, benzoicacids carrying a sulfoxide cannot be converted directly into their acidchlorides. Here, it is advisable to prepare initially, at the thioetherstage, the amide and then to oxidize the thioether to the sulfoxide.

Collections of compounds of the formula (I) and/or salts thereof whichcan be synthesized by the abovementioned reactions can also be preparedin a parallelized manner, in which case this may be accomplished in amanual, partly automated or fully automated manner. It is possible, forexample, to automate the conduct of the reaction, the work-up or thepurification of the products and/or intermediates. Overall, this isunderstood to mean a procedure as described, for example, by D. Tiebesin Combinatorial Chemistry—Synthesis, Analysis, Screening (editorGünther Jung), Wiley, 1999, on pages 1 to 34.

For the parallelized conduct of the reaction and workup, it is possibleto use a number of commercially available instruments, for exampleCalypso reaction blocks from Barnstead International, Dubuque, Iowa52004-0797, USA or reaction stations from Radleys, Shirehill, SaffronWalden, Essex, CB11 3AZ, England, or MuItiPROBE Automated Workstationsfrom PerkinElmer, Waltham, Mass. 02451, USA. For the parallelizedpurification of compounds of the general formula (I) and salts thereofor of intermediates which occur in the course of preparation, availableapparatuses include chromatography apparatuses, for example from ISCO,Inc., 4700 Superior Street, Lincoln, Nebr. 68504, USA.

The apparatuses detailed lead to a modular procedure in which theindividual working steps are automated, but manual operations have to becarried out between the working steps. This can be circumvented by usingpartly or fully integrated automation systems in which the respectiveautomation modules are operated, for example, by robots. Automationsystems of this type can be obtained, for example, from Caliper,Hopkinton, Mass. 01748, USA.

The implementation of single or multiple synthesis steps can besupported by the use of polymer-supported reagents/scavenger resins. Thespecialist literature describes a series of experimental protocols, forexample in ChemFiles, Vol. 4, No. 1, Polymer-Supported Scavengers andReagents for Solution-Phase Synthesis (Sigma-Aldrich).

Aside from the methods described here, the compounds of the generalformula (I) and salts thereof can be prepared completely or partially bysolid-phase-supported methods. For this purpose, individualintermediates or all intermediates in the synthesis or a synthesisadapted for the corresponding procedure are bound to a synthesis resin.Solid-phase-supported synthesis methods are described adequately in thetechnical literature, for example Barry A. Bunin in “The CombinatorialIndex”, Academic Press, 1998 and Combinatorial Chemistry—Synthesis,Analysis, Screening (editor Gunther Jung), Wiley, 1999. The use ofsolid-phase-supported synthesis methods permits a number of protocols,which are known from the literature and which for their part may beperformed manually or in an automated manner. The reactions can beperformed, for example, by means of IRORI technology in microreactorsfrom Nexus Biosystems, 12140 Community Road, Poway, Calif. 92064, USA.

Both in the solid and in the liquid phase, individual or severalsynthesis steps may be supported by the use of microwave technology. Thespecialist literature describes a series of experimental protocols, forexample in Microwaves in Organic and Medicinal Chemistry (editor C. O.Kappe and A. Stadler), Wiley, 2005.

The preparation by the processes described here gives compounds of theformula (I) and salts thereof in the form of substance collections,which are called libraries. The present invention also provideslibraries comprising at least two compounds of the formula (I) and saltsthereof.

The compounds of the formula (I) according to the invention (and/orsalts thereof), collectively referred to hereinafter as “compoundsaccording to the invention”, have excellent herbicidal efficacy againsta broad spectrum of economically important monocotyledonous anddicotyledonous annual harmful plants. The active compounds also havegood control over perennial harmful plants which are difficult tocontrol and produce shoots from rhizomes, root stocks or other perennialorgans.

The present invention therefore also provides a method for controllingunwanted plants or for regulating the growth of plants, preferably inplant crops, in which one or more compound(s) according to the inventionis/are applied to the plants (for example harmful plants such asmonocotyledonous or dicotyledonous weeds or unwanted crop plants), theseed (for example grains, seeds or vegetative propagules such as tubersor shoot parts with buds) or the area on which the plants grow (forexample the area under cultivation). The compounds according to theinvention can be deployed, for example, prior to sowing (if appropriatealso by incorporation into the soil), prior to emergence or afteremergence. Specific examples of some representatives of themonocotyledonous and dicotyledonous weed flora which can be controlledby the compounds according to the invention are as follows, though theenumeration is not intended to impose a restriction to particularspecies.

Monocotyledonous harmful plants of the genera: Aegilops, Agropyron,Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus,Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa,Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis,Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria,Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria,Scirpus, Setaria, Sorghum.

Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia,Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella,Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura,Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium,Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria,Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago,Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex,Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola,Xanthium.

When the compounds according to the invention are applied to the soilsurface before germination, either the weed seedlings are preventedcompletely from emerging or the weeds grow until they have reached thecotyledon stage, but then stop growing and eventually, after three tofour weeks have elapsed, die completely.

If the active compounds are applied post-emergence to the green parts ofthe plants, growth stops after the treatment, and the harmful plantsremain at the growth stage at the time of application, or they diecompletely after a certain time, so that in this manner competition bythe weeds, which is harmful to the crop plants, is eliminated very earlyand in a lasting manner.

Although the compounds according to the invention display an outstandingherbicidal activity against monocotyledonous and dicotyledonous weeds,crop plants of economically important crops, for example dicotyledonouscrops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita,Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum,Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, ormonocotyledonous crops of the genera Allium, Ananas, Asparagus, Avena,Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale,Triticum, Zea, in particular Zea and Triticum, are damaged only to aninsignificant extent, or not at all, depending on the structure of therespective compound according to the invention and its application rate.For these reasons, the present compounds are very suitable for theselective control of unwanted plant growth in plant crops such asagriculturally useful plants or ornamentals.

In addition, the compounds according to the invention (depending ontheir particular structure and the application rate deployed) haveoutstanding growth-regulating properties in crop plants. They interveneto regulate the plant's metabolism and can thus be used for controlledinfluence on plant constituents and to facilitate harvesting, forexample by triggering desiccation and stunted growth. In addition, theyare also suitable for general control and inhibition of unwantedvegetative growth without killing the plants in the process. Inhibitingvegetative growth plays a major role for many monocotyledonous anddicotyledonous crops, since, for example, this can reduce or completelyprevent lodging.

By virtue of their herbicidal and plant-growth-regulating properties,the active compounds can also be used for controlling harmful plants incrops of genetically modified plants or plants modified by conventionalmutagenesis. In general, transgenic plants are notable for specialadvantageous properties, for example for resistances to certainpesticides, in particular certain herbicides, resistances to plantdiseases or organisms that cause plant diseases, such as certain insectsor microorganisms such as fungi, bacteria or viruses. Other particularproperties relate, for example, to the harvested material with regard toquantity, quality, storability, composition and specific constituents.For instance, there are known transgenic plants with an elevated starchcontent or altered starch quality, or those with a different fatty acidcomposition in the harvested material.

It is preferred, with respect to transgenic crops, to use the compoundsaccording to the invention in economically important transgenic crops ofuseful plants and ornamentals, for example of cereals such as wheat,barley, rye, oats, millet/sorghum, rice and corn or else crops of sugarbeet, cotton, soybean, oilseed rape, potato, tomato, peas and othervegetables. It is preferred to employ the compounds according to theinvention as herbicides in crops of useful plants which are resistant,or have been made resistant by recombinant means, to the phytotoxiceffects of the herbicides.

Preference is given to the use of the compounds according to theinvention or salts thereof in economically important transgenic crops ofuseful plants and ornamentals, for example of cereals such as wheat,barley, rye, oats, millet/sorghum, rice, cassava and corn, or else cropsof sugar beet, cotton, soybean, oilseed rape, potato, tomato, peas andother vegetables. Preferably, the compounds according to the inventioncan be used as herbicides in crops of useful plants which are resistant,or have been made resistant by recombinant means, to the phytotoxiceffects of the herbicides.

Conventional ways of producing novel plants which have modifiedproperties in comparison to plants which have occurred to date consist,for example, in traditional breeding methods and the generation ofmutants. Alternatively, novel plants with modified properties can begenerated with the aid of recombinant methods (see, for example,EP-A-0221044, EP-A-0131624). For example, there have been manydescriptions of

-   -   recombinant modifications of crop plants for the purpose of        modifying the starch synthesized in the plants (e.g. WO        92/11376, WO 92/14827, WO 91/19806),    -   transgenic crop plants which are resistant to particular        herbicides of the glufosinate type (cf., for example,        EP-A-0242236, EP-A-242246) or glyphosate type (WO 92/00377) or        of the sulfonylurea type (EP-A-0257993, U.S. Pat. No.        5,013,659),    -   transgenic crop plants, for example cotton, with the ability to        produce Bacillus thuringiensis toxins (Bt toxins) which make the        plants resistant to particular pests (EP-A-0142924,        EP-A-0193259).    -   transgenic crop plants with a modified fatty acid composition        (WO 91/13972).    -   genetically modified crop plants with novel constituents or        secondary metabolites, for example novel phytoalexins, which        bring about an increased disease resistance (EPA 309862,        EPA0464461)    -   genetically modified plants with reduced photorespiration which        feature higher yields and higher stress tolerance (EPA 0305398).    -   transgenic crop plants which produce pharmaceutically or        diagnostically important proteins (“molecular pharming”)    -   transgenic crop plants which feature higher yields or better        quality    -   transgenic crop plants which are distinguished by a combination,        for example, of the abovementioned novel properties (“gene        stacking”)

A large number of molecular-biological techniques by means of whichnovel transgenic plants with modified properties can be generated areknown in principle; see, for example, I. Potrykus and G. Spangenberg(eds.) Gene Transfer to Plants, Springer Lab Manual (1995), SpringerVerlag Berlin, Heidelberg, or Christou, “Trends in Plant Science” 1(1996) 423-431.

For such recombinant manipulations, nucleic acid molecules which allowmutagenesis or a sequence change by recombination of DNA sequences canbe introduced into plasmids. With the aid of standard methods, it ispossible, for example, to undertake base exchanges, remove parts ofsequences or add natural or synthetic sequences. For the joining of theDNA fragments to one another, adaptors or linkers can be attached to thefragments; see, for example, Sambrook et al., 1989, Molecular Cloning, ALaboratory Manual, 2nd ed. Cold Spring Harbor Laboratory Press, ColdSpring Harbor, N.Y.; or Winnacker “Gene and Klone” [Genes and Clones],VCH Weinheim 2nd edition 1996.

For example, the generation of plant cells with a reduced activity of agene product can be achieved by expressing at least one correspondingantisense RNA, a sense RNA for achieving a cosuppression effect, or byexpressing at least one suitably constructed ribozyme which specificallycleaves transcripts of the abovementioned gene product. To this end, itis possible firstly to use DNA molecules which encompass the entirecoding sequence of a gene product inclusive of any flanking sequenceswhich may be present, and also DNA molecules which only encompassportions of the coding sequence, it being necessary for these portionsto be long enough to have an antisense effect in the cells. It is alsopossible to use DNA sequences which have a high degree of homology tothe coding sequences of a gene product, but are not completelyidentical.

When expressing nucleic acid molecules in plants, the proteinsynthesized can be localized in any desired compartment of the plantcell. However, in order to achieve localization in a particularcompartment, it is possible, for example, to join the coding region toDNA sequences which ensure localization in a particular compartment.Such sequences are known to those skilled in the art (see, for example,Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl.Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991),95-106). The nucleic acid molecules can also be expressed in theorganelles of the plant cells.

The transgenic plant cells can be regenerated by known techniques togive whole plants. In principle, the transgenic plants may be plants ofany desired plant species, i.e. both monocotyledonous and dicotyledonousplants.

For instance, it is possible to obtain transgenic plants whoseproperties are altered by overexpression, suppression or inhibition ofhomologous (=natural) genes or gene sequences, or expression ofheterologous (=foreign) genes or gene sequences.

Preferably, the compounds according to the invention can be used intransgenic crops which are resistant to growth regulators, for exampledicamba, or to herbicides which inhibit essential plant enzymes, forexample acetolactate synthases (ALS), EPSP synthases, glutaminesynthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD), or toherbicides from the group of the sulfonylureas, the glyphosates,glufosinates or benzoylisoxazoles and analogous active compounds.

On employment of the active compounds according to the invention intransgenic crops, not only do the effects toward harmful plants to beobserved in other crops occur, but often also effects which are specificto application in the particular transgenic crop, for example an alteredor specifically widened spectrum of weeds which can be controlled,altered application rates which can be used for the application,preferably good combinability with the herbicides to which thetransgenic crop is resistant, and influencing of growth and yield of thetransgenic crop plants.

The invention therefore also provides for the use of the compoundsaccording to the invention as herbicides for control of harmful plantsin transgenic crop plants.

The compounds according to the invention can be applied in the form ofwettable powders, emulsifiable concentrates, sprayable solutions,dusting products or granules in the customary formulations. Theinvention therefore also provides herbicidal and plant-growth-regulatingcompositions which comprise the compounds according to the invention.

The compounds according to the invention can be formulated in variousways, according to the biological and/or physicochemical parametersrequired. Examples of possible formulations include: wettable powders(WP), water-soluble powders (SP), water-soluble concentrates,emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water andwater-in-oil emulsions, sprayable solutions, suspension concentrates(SC), oil- or water-based dispersions, oil-miscible solutions, capsulesuspensions (CS), dusting products (DP), seed-dressing products,granules for broadcasting and soil application, granules (GR) in theform of microgranules, sprayable granules, coated granules andadsorption granules, water-dispersible granules (WG), water-solublegranules (SG), ULV formulations, microcapsules and waxes.

These individual formulation types are known in principle and aredescribed, for example, in: Winnacker-Küchler, “Chemische Technologie”[Chemical Technology], volume 7, C. Hanser Verlag Munich, 4th ed. 1986;Wade van Valkenburg, “Pesticide Formulations”, Marcel Dekker, N.Y.,1973; K. Martens, “Spray Drying” Handbook, 3rd ed. 1979, G. Goodwin Ltd.London.

The necessary formulation assistants, such as inert materials,surfactants, solvents and further additives, are likewise known and aredescribed, for example, in: Watkins, “Handbook of Insecticide DustDiluents and Carriers”, 2nd ed., Darland Books, Caldwell N.J., H.v.Olphen, “Introduction to Clay Colloid Chemistry”; 2nd ed., J. Wiley &Sons, N.Y.; C. Marsden, “Solvents Guide”; 2nd ed., Interscience, N.Y.1963; McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ. Corp.,Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface ActiveAgents”, Chem. Publ. Co. Inc., N.Y. 1964; Schonfeldt,“Grenzflachenaktive Athylenoxidaddukte” [Interface-active Ethylene OxideAdducts], Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Kuchler,“Chemische Technologie” [Chemical Technology], volume 7, C. HanserVerlag Munich, 4th ed. 1986.

Based on these formulations, it is also possible to produce combinationswith other pesticidally active substances, such as, for example,insecticides, acaricides, herbicides, fungicides, and also withsafeners, fertilizers and/or growth regulators, for example in the formof a finished formulation or as a tank mix. Suitable safeners are, forexample, mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl,cloquintocet-mexyl and dichlormid.

Wettable powders are preparations which can be dispersed uniformly inwater and, in addition to the active ingredient, apart from a diluent orinert substance, also comprise surfactants of the ionic and/or nonionictype (wetting agents, dispersants), for example polyoxyethylatedalkylphenols, polyethoxylated fatty alcohols, polyoxyethylated fattyamines, fatty alcohol polyglycol ether sulfates, alkanesulfonates,alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2′dinaphthylmethane-6,6′-disulfonate, sodium dibutylnaphthalenesulfonateor else sodium oleoylmethyltaurate. To prepare the wettable powders, theherbicidally active compounds are ground finely, for example incustomary apparatus such as hammer mills, blower mills and air-jetmills, and simultaneously or subsequently mixed with the formulationauxiliaries.

Emulsifiable concentrates are produced by dissolving the active compoundin an organic solvent, for example butanol, cyclohexanone,dimethylformamide, xylene, or else relatively high-boiling aromatics orhydrocarbons or mixtures of the organic solvents, with addition of oneor more ionic and/or nonionic surfactants (emulsifiers). Emulsifiersused may, for example, be: calcium alkylarylsulfonates such as calciumdodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acidpolyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycolethers, propylene oxide-ethylene oxide condensation products, alkylpolyethers, sorbitan esters, for example sorbitan fatty acid esters, orpolyoxyethylene sorbitan esters, for example polyoxyethylene sorbitanfatty acid esters.

Dusts are obtained by grinding the active compound with finelydistributed solid substances, for example talc, natural clays, such askaolin, bentonite and pyrophyllite, or diatomaceous earth.

Suspension concentrates may be water- or oil-based. They can beproduced, for example, by wet grinding by means of commercial bead millswith optional addition of surfactants as already listed above, forexample, for the other formulation types.

Emulsions, for example oil-in-water emulsions (EW), can be produced, forexample, by means of stirrers, colloid mills and/or static mixers usingaqueous organic solvents and optionally surfactants as already listedabove, for example, for the other formulation types.

Granules can be prepared either by spraying the active compound ontoadsorptive granular inert material or by applying active compoundconcentrates to the surface of carriers, such as sand, kaolinites orgranular inert material, by means of adhesives, for example polyvinylalcohol, sodium polyacrylates or else mineral oils. Suitable activecompounds can also be granulated in the manner customary for theproduction of fertilizer granules—if desired as a mixture withfertilizers.

Water-dispersible granules are prepared generally by the customaryprocesses such as spray-drying, fluidized bed granulation, pangranulation, mixing with high-speed mixers and extrusion without solidinert material.

For the production of pan granules, fluidized bed granules, extrudergranules and spray granules, see, for example, processes in“Spray-Drying Handbook” 3rd ed. 1979, G. Goodwin Ltd., London, J. E.Browning, “Agglomeration”, Chemical and Engineering 1967, pages 147 ff.;“Perry's Chemical Engineer's Handbook”, 5th ed., McGraw-Hill, New York1973, pp. 8-57.

For further details regarding the formulation of crop protection agents,see, for example, G. C. Klingman, “Weed Control as a Science”, JohnWiley and Sons, Inc., New York, 1961, pages 81-96 and J. D. Freyer, S.A. Evans, “Weed Control Handbook”, 5th ed., Blackwell ScientificPublications, Oxford, 1968, pages 101-103.

The agrochemical preparations contain generally 0.1 to 99% by weight,especially 0.1 to 95% by weight, of compounds according to theinvention.

In wettable powders, the active compound concentration is, for example,about 10 to 90% by weight, the remainder to 100% by weight consisting ofcustomary formulation constituents. In emulsifiable concentrates, theactive compound concentration may be about 1 to 90% and preferably 5 to80% by weight. Formulations in the form of dusts comprise 1 to 30% byweight of active compound, preferably usually 5 to 20% by weight ofactive compound; sprayable solutions contain about 0.05 to 80% andpreferably 2 to 50% by weight of active compound. In the case ofwater-dispersible granules, the active compound content depends partlyon whether the active compound is present in liquid or solid form and onwhich granulation assistants, fillers, etc., are used. In thewater-dispersible granules, the content of active compound is, forexample, between 1 and 95% by weight, preferably between 10 and 80% byweight.

In addition, the active compound formulations mentioned optionallycomprise the respective customary tackifiers, wetting agents,dispersants, emulsifiers, penetrants, preservatives, antifreeze agentsand solvents, fillers, carriers and dyes, defoamers, evaporationinhibitors and agents which influence the pH and the viscosity.

Based on these formulations, it is also possible to produce combinationswith other pesticidally active substances, such as, for example,insecticides, acaricides, herbicides, fungicides, and also withsafeners, fertilizers and/or growth regulators, for example in the formof a finished formulation or as a tank mix.

For application, the formulations in commercial form are, ifappropriate, diluted in a customary manner, for example in the case ofwettable powders, emulsifiable concentrates, dispersions andwater-dispersible granules with water. Preparations in the form ofdusts, granules for soil application or granules for sowing andsprayable solutions are usually not diluted further with other inertsubstances prior to application.

The required application rate of the compounds of the formula (I) varieswith the external conditions, including temperature, humidity and thetype of herbicide used. It can vary within wide limits, for examplebetween 0.001 and 1.0 kg/ha or more of active substance, but it ispreferably between 0.005 and 750 g/ha.

The examples below illustrate the invention.

A. CHEMICAL EXAMPLES Synthesis of2-methyl-3-methylsulfonyl-4-trifluorometyl-N-(1-propyltetrazol-5-yl)thiobenzamide(No. 1-9)

196 mg (0.5 mmol) of2-methyl-3-methylsulfonyl-4-trifluorometyl-N-(1-propyltetrazol-5-yl)benzamideand 404 mg (1 mmol) of Lawesson's reagent in 5 ml of dioxane are heatedunder reflux for 5 h. After the end of the reaction, 1 ml of water isadded, the mixture is concentrated and the residue is purifiedchromatographically by HPLC, giving 158 mg of2-methyl-3-methylsulfonyl-4-trifluorometyl-N-(1-propyltetrazol-5-yl)thiobenzamide(yield: 78%).

The examples listed in the tables below were prepared analogously to theabovementioned methods or are obtainable analogously to theabovementioned methods. The compounds listed in the tables below arevery particularly preferred.

The abbreviations used mean:

Et=ethyl Me=methyl n-Pr=n-propyl c-Pr=c-propyl

TABLE 1 Compounds of the general formula (I) in which A represents CYand B represents N and W represents hydrogen

Physical data (¹H-NMR, DMSO-d₆, 400 Ex. No. R X Y Z MHz) 1-1 Me Cl HSO₂Me 1-2 Me SO₂Me H CF₃ 8.26 (s, 1H), 8.23 (d, 1H), 7.89 (d, 1H), 4.08(s, 3H), 3.48 (s, 3H) 1-3 Me Me SMe CF₃ 1-4 MeOC₂H₄ Me SMe CF₃ 1-5 Me MeSOMe CF₃ 1-6 Et Me SOMe CF₃ 1-7 Me Me SO₂Me CF₃ 8.00 (d, 1H), 7.94 (d,1H), 4.05 (s, 3H), 3.44 (s, 3H), 2.78 (s, 3H) 1-8 Et Me SO₂Me CF₃ 7.99(d, 1H), 7.92 (d, 1H), 4.36 (q, 2H), 3.43 (s, 3H), 2.79 (s, 3H), 1.49(t, 3H) 1-9 Pr Me SO₂Me CF₃ 7.99 (d, 1H), 7.90 (d, 1H), 4.29 (t, 2H),3.43 (s, 3H), 2.79 (s, 3H), 1.90 (m, 2H), 0.89 (t, 3H) 1-10 MeOC₂H₄ MeSO₂Me CF₃ 1-11 Me Me SEt CF₃ 1-12 Et Me SEt CF₃ 1-13 Me Me SOEt CF₃ 1-14Et Me SOEt CF₃ 1-15 Me Me SO₂Et CF₃ 1-16 Et Me SO₂Et CF₃ 1-17 Me MeSO₂Me Cl 1-18 Me Me SEt Cl 1-19 Me Me SOEt Cl 1-20 Et Me SOEt Cl 1-21 MeMe SO₂Et Cl 1-22 Me Me SMe Br 1-23 Me Me SEt Br 1-24 Me Me4,5-dihydro-1,2-oxazol-3-yl SO₂Me 1-25 Et Me 4,5-dihydro-1,2-oxazol-3-ylSO₂Me 1-26 Me Me pyrazol-1-yl SO₂Me 8.07 (d, 1H), 7.78 (d, 1H), 7.91 (d,1H), 7.86 (d, 1H), 6.60 (t, 1H), 4.04 (s, 3H), 3.03 (s, 3H), 1.92 (s,3H) 1-27 Et Me pyrazol-1-yl SO₂Me 1-28 Et Me F SO₂Me 13.0 (brs, 1H),7.80 (t, 1H), 7.56 (d, 1H), 4.35 (q, 3H), 3.38 (s, 3H), 2.39 (s, 3H),1.50 (t, 3H) 1-29 Me Me Cl SO₂Me 12.8 (brs, 1H), 8.01 (d, 1H), 7.70 (d,1H), 4.05 (s, 3H), 3.43 (s, 3H), 2.49 (s, 3H) 1-30 Me Me OMe SO₂Me 7.79(d, 1H), 7.36 (d, 1H), 4.10 (s, 3H), 3.95 (s, 3H), 3.23 (s, 3H), 2.47(s, 3H) 1-31 Me Me SMe SO₂Me 1-32 Me Me SO₂Me SO₂Me 1-33 Et Me SO₂MeSO₂Me 1-34 Me Me SO₂Et SO₂Me 1-35 Et Me SO₂Et SO₂Me 1-36 Me Et SMe CF₃1-37 Me Et SOMe CF₃ 1-38 Me Et SO₂Me CF₃ 1-39 Me Et SMe Cl 1-40 Et EtSMe Cl 1-41 Me Et SOMe Cl 1-42 Me Et SMe Br 1-43 Me Et SO₂Me Br 1-44 MePr SMe CF₃ 1-45 Me Pr SOMe CF₃ 1-46 Me c-Pr SMe CF₃ 1-47 Me OMe SMe CHF₂1-48 Et OMe SMe CHF₂ 1-49 Me OMe SOMe CHF₂ 1-50 Et OMe SOMe CHF₂ 1-51 MeOMe SO₂Me CHF₂ 1-52 Et OMe SO₂Me CHF₂ 1-53 Me OMe SEt CHF₂ 1-54 Me OMeSMe CF₃ 12.95 (brs, 1H), 7.73 (d, 1H), 7.66 (d, 1H), 4.04 (s, 3H), 3.98(s, 3H), 2.48 (s, 3H) 1-55 Et OMe SMe CF₃ 1-56 Me OMe SOMe CF₃ 1-57 EtOMe SOMe CF₃ 1-58 Me OMe SO₂Me CF₃ 1-59 Et OMe SO₂Me CF₃ 1-60 Me OMe SEtCF₃ 1-61 Me Cl SMe H 1-62 Me Cl SMe Me 1-63 Me Cl SO₂Me Me 7.65 (d, 1H),7.34 (d, 1H), 4.10 (s, 3H), 3.32 (s, 3H), 2.79 (s, 3H) 1-64 Me Cl SO₂EtMe 1-65 Me Cl SO₂Me CF₃ 1-66 Me Cl OC₂H₄OMe Cl 1-67 Me Cl SMe Cl 1-68 EtCl SMe Cl 1-69 Me Cl SOMe Cl 1-70 Et Cl SOMe Cl 1-71 Me Cl SO₂Me Cl 1-72Et Cl SO₂Me Cl 1-73 Me Cl SO₂Et Cl 1-74 Me Cl CH₂OMe SO₂Me 8.05 (d, 1H),7.65 (d, 1H), 5.07 (s, 2H), 4.09 (s, 3H), 3.51 (s, 3H), 3.24 (s, 3H)1-75 Me Cl CH₂OCH₂CF₃ SO₂Me 13.2 (brs, 1H), 8.09 (d, 1H), 7.91 (d, 1H),5.26 (s, 2H), 4.31 (q, 2H), 4.05 (s, 3H), 3.37 (s, 3H) 1-76 Et ClCH₂OCH₂CF₃ SO₂Me 1-77 Me Cl CH₂OC₂H₄OMe SO₂Me 1-78 Me Cl4,5-dihydro-1,2-oxazol-3-yl SO₂Me 1-79 Me Cl 4,5-dihydro-1,2-oxazol-3-ylSO₂Et 1-80 Me Cl 5-methoxymethy-4,5- SO₂Et dihydro-1,2-oxazol-3-yl 1-81Me Cl OMe SO₂Me 7.93 (d, 1H), 7.48 (d, 1H), 4.11 (s, 3H), 4.10 (s, 3H),3.26 (s, 3H) 1-82 Me Cl OMe SO₂Et 1-83 Me Cl OEt SO₂Me 7.94 (d, 1H),7.46 (d, 1H), 4.34 (q, 2H), 4.10 (s, 3H), 3.28 (s, 3H), 1.53 (t, 3H)1-84 Me Cl OEt SO₂Et 1-85 Me Cl OPr SO₂Me 1-86 Me Cl OPr SO₂Et 1-87 MeCl Oi-Bu SO₂Me 1-88 Me Cl OCH₂c-Pr SO₂Me 7.93 (d, 1H), 7.46 (d, 1H),4.11 (d, 2H), 4.09 (s, 3H), 3.32 (s, 3H), 1.40-1.55 (m, 1H), 0.64-0.71(m, 2H), 0.43-0.50 (m, 2H) 1-89 Me Cl OCH₂c-Pr SO₂Et 1-90 Me Cl OC₂H₄OMeSO₂Me 1-91 Me Cl OC₃H₆OMe SO₂Me 7.92 (d, 1H), 7.47 (d, 1H), 4.35 (t, 2H)4.10 (s, 3H), 3.62 (t, 2H), 3.37 (s, 3H), 3.26 (s, 3H), 2.18 (quin, 2H)1-92 Me Cl SMe SO₂Me

TABLE 2 Compounds of the general formula (I) in which A represents CYand B represents CH and W represents hydrogen

Physical data (¹H-NMR, DMSO-d₆, 400 Ex. No. R X Y Z MHz) 2-1 Me Me SO₂MeCF₃ 2-2 Me Me 4,5-dihydro-1,2-oxazol-3-yl SO₂Me 2-3 Me Me pyrazol-1-ylSO₂Me 2-4 Me Me SO₂Me SO₂Me 8.20 (brs, 1H, 8.19 (d, 1H), 7.88 (brs, 1H),3.79 (s, 3H), 3.58 (s, 3H), 3.56 (s, 3H), 2.71 (s, 3H) 2-5 Me Cl SO₂MeCl 2-6 Me Cl 4,5-dihydro-1,2-oxazol-3-yl SO₂Me 2-7 Me Cl4,5-dihydro-1,2-oxazol-3-yl SO₂Et 2-8 Me Cl OC₂H₄OMe SO₂Me

TABLE 3 Compounds of the general formula (I) in which A represents CYand B represents N

Physical data (¹H-NMR, DMSO-d₆, Ex. No. R X Y Z W 400 MHz) 3-1 Me Cl HSMe Me 12.85 (brs, 1H), 7.47 (s, 1H), 7.27 (s, 1H), 4.02 (s, 3H), 2.56(s, 3H), 2.26 (s, 3H) 3-2 Me Cl SMe H Me 3-3 Me Cl SO₂Me H Me 3-4 Et ClSO₂Me H Me 3-5 Me Cl Me SMe Me 3-6 Et Cl Me SO₂Me Me 3-7 Me Br SO₂Me HMe 3-8 Me Cl OMe SMe OMe

TABLE 4 Compounds of the general formula (I) in which A and B eachrepresent N and W represents hydrogen

Physical data Ex. No. R X Z (¹H-NMR, DMSO-d₆, 400 MHz) 4-1 Me Me CF₃13.1 (brs, 1H), 8.17 (d, 1H), 7.88 (d, 1H), 4.06 (s, 3H), 2.68 (s, 3H)4-2 Me CH₂OMe CF₃ 13.1 (brs, 1H), 8.25 (d, 1H), 8.02 (d, 1H), 4.79 (s,2H), 4.05 (s, 3H), 3.17 (s, 3H) 4-3 Et CH₂OMe CF₃ 4-4 Me CH₂OC₂H₄OMe CF₃4-5 Et CH₂OC₂H₄OMe CF₃ 4-6 Me CH₂OCH₂c-Pr CF₃ 4-7 Me Cl CF₃ 8.38 (d,1H), 8.09 (d, 1H), 4.03 (s, 3H) 4-8 Me Br CF₃ 4-9 Me SO₂Me CF₃ 4-10 MeSMe SMe 7.73 (d, 1H), 7.12 (d, 1H), 4.02 (s, 3H), 2.60 (s, 3H), 2.54 (s,3H)

B. FORMULATION EXAMPLES

-   a) A dusting product is obtained by mixing 10 parts by weight of a    compound of the formula (I) and/or salts thereof and 90 parts by    weight of talc as an inert substance and comminuting the mixture in    a hammer mill.-   b) A readily water-dispersible, wettable powder is obtained by    mixing 25 parts by weight of a compound of the formula (I) and/or    salts thereof, 64 parts by weight of kaolin-containing quartz as an    inert substance, 10 parts by weight of potassium lignosulfonate and    1 part by weight of sodium oleoylmethyltaurate as a wetting agent    and dispersant, and grinding the mixture in a pinned-disk mill.-   c) A readily water-dispersible dispersion concentrate is obtained by    mixing 20 parts by weight of a compound of the formula (I) and/or    salts thereof with 6 parts by weight of alkylphenol polyglycol ether    (®Triton X 207), 3 parts by weight of isotridecanol polyglycol ether    (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling    range for example about 255 to above 277 C), and grinding the    mixture in a ball mill to a fineness of below 5 microns.-   d) An emulsifiable concentrate is obtained from 15 parts by weight    of a compound of the formula (I) and/or salts thereof, 75 parts by    weight of cyclohexanone as a solvent and 10 parts by weight of    ethoxylated nonylphenol as an emulsifier.-   e) Water-dispersible granules are obtained by mixing    -   75 parts by weight of a compound of the formula (I) and/or salts        thereof,    -   10 parts by weight of calcium lignosulfonate,    -   5 parts by weight of sodium laurylsulfate,    -   3 parts by weight of polyvinyl alcohol and    -   7 parts by weight of kaolin,    -   grinding the mixture in a pinned-disk mill and granulating the        powder in a fluidized bed by spraying on water as a granulating        liquid.-   f) Water-dispersible granules are also obtained by homogenizing and    precomminuting    -   25 parts by weight of a compound of the formula (I) and/or salts        thereof,    -   5 parts by weight of sodium        2,2′-dinaphthylmethane-6,6′-disulfonate,    -   2 parts by weight of sodium oleoylmethyltaurate,    -   1 part by weight of polyvinyl alcohol,    -   17 parts by weight of calcium carbonate and    -   50 parts by weight of water    -   in a colloid mill, then grinding the mixture in a bead mill and        atomizing and drying the resulting suspension in a spray tower        by means of a one-phase nozzle.

C. BIOLOGICAL EXAMPLES 1. Pre-Emergence Herbicidal Action AgainstHarmful Plants

Seeds of monocotyledonous and dicotyledonous weed plants and crop plantsare placed in wood-fiber pots in sandy loam and covered with soil. Thecompounds according to the invention, formulated in the form of wettablepowders (WP) or as emulsion concentrates (EC), are then applied asaqueous suspension or emulsion at a water application rate of 600 to 800I/ha (converted) with the addition of 0.2% of wetting agent to thesurface of the covering soil. After the treatment, the pots are placedin a greenhouse and kept under good growth conditions for the testplants. The damage to the test plants is assessed visually after a testperiod of 3 weeks by comparison with untreated controls (herbicidalactivity in percent (%): 100% action=the plants have died, 0%action=like control plants). Here, for example, the compounds Nos 1-8,1-26 and 4-7, at an application rate of 80 g/ha, show an activity of atleast 80% against Alopecurus myosuroides, Avena fatua, Cyperusserotinus, Echinochloa crus galli, Lolium multiflorum, Setaria viridis,Abutilon theophrasti, Amaranthus retroflexus, Matricaria inodora,Pharbitis purpureum, Stellaria media, Viola tricolor and Veronicapersica.

2. Post-Emergence Herbicidal Action Against Harmful Plants

Seeds of monocotyledonous and dicotyledonous weed and crop plants areplaced in sandy loam in wood-fiber pots, covered with soil andcultivated in a greenhouse under good growth conditions. 2 to 3 weeksafter sowing, the test plants are treated at the one-leaf stage. Thecompounds according to the invention, formulated in the form of wettablepowders (WP) or as emulsion concentrates (EC), are then sprayed asaqueous suspension or emulsion at a water application rate of 600 to 800I/ha (converted) with the addition of 0.2% of wetting agent onto thegreen parts of the plants. After the test plants have been left to standin the greenhouse under optimal growth conditions for about 3 weeks, theaction of the preparations is assessed visually in comparison tountreated controls (herbicidal action in percent (%): 100% action=theplants have died, 0% action=like control plants). Here, for example, thecompounds Nos 1-8 and 1-83, at an application rate of 80 g/ha, show anactivity of at least 80% against Alopecurus myosuroides, Avena fatua,Cyperus serotinus, Echinochloa crus galli, Lolium multiflorum, Setariaviridis, Abutilon theophrasti, Amaranthus retroflexus, Matricariainodora, Pharbitis purpureum, Polygonum convolvulus, Stellaria media,Viola tricolor and Veronica persica.

3. Comparative Tests

To demonstrate the superiority of the compounds according to theinvention, numerous compounds according to the invention were comparedin an exemplary manner to the structurally closest compounds, known fromWO 2012/028579 A1, at various application rates and with differentharmful plants and crop plants. These comparative experiments werecarried out under the conditions mentioned above by the pre-emergencemethod and the post-emergence method. In the tables below, the top linein each case states the compound according to the invention, and thebottom line states the compound from WO 2012/028579 A1.

The abbreviations used here mean:

Harmful plants ABUTH Abutilon ALOMY Alopecurus theophrasti myosuroidesAMARE Amaranthus AVEFA Avena retroflexus fatua CYPES Cyperus ECHCGEchinochloa serotinus crus galli LOLMU Lolium PHBPU Pharbitismultiflorum purpureum POLCO Polygonum SETVI Setaria convolvulus viridisCrop plants BRSNW Brassica napus ORYSA Oryza sativa (oilseed rape)(rice) TRZAS Triticum aestivum ZEAMX Zea mays (wheat) (corn)

TABLE A Pre-emergence action Damage to crop Herbicidal efficacy Dosageplants against Compound [g/ha] BRSNW ABUTH PHBPU

20  0% 90% 20%

20 20% 70%  0%

TABLE B Pre-emergence action Damage to crop Herbicidal efficacy Dosageplants against Compound [g/ha] ORYSA CYPES ECHCG

20  0% 100% 20%

20 50%  0%  0%

TABLE C Pre-emergence action Damage to crop Herbicidal efficacy Dosageplants against Compound [g/ha] ZEAMX AVEFA POLCO

320  0% 90% 90%

320 20% 70% 50%

TABLE D Pre-emergence action Damage to crop Herbicidal efficacy Dosageplants against Compound [g/ha] TRZAS PHBPU POLCO

320  0% 80% 80%

320 20% 60% 60%

TABLE E Pre-emergence action Damage to crop Herbicidal efficacy Dosageplants against Compound [g/ha] BRSNW ABUTH AMARE

320  0% 80% 90%

320 20%  0% 40%

TABLE F Pre-emergence action Herbicidal efficacy Dosage Damage to cropplants against Compound [g/ha] BRSNW ORYSA ECHCG POLCO

20  0% 20% 100% 60%

20 30% 50%  20%  0%

TABLE G Post-emergence action Herbicidal efficacy Dosage Damage to cropplants against Compound [g/ha] ORYSA TRZAS PHBPU POLCO

5 10%  0% 80% 60%

5 40% 30% 20% 40%

TABLE H Post-emergence action Dosage Herbicidal efficacy againstCompound [g/ha] ECHCG SETVI AMARE

5 70% 40% 40%

5 10%  0% 20%

TABLE I Post-emergence action Damage to crop Herbicidal efficacy Dosageplants against Compound [g/ha] ZEAMX ALOMY LOLMU

80  0% 80% 20%

80 20% 30%  0%

TABLE J Post-emergence action Damage to crop Herbicidal efficacy Dosageplants against Compound [g/ha] TRZAS POLCO

80 20% 90%

80 60% 70%

TABLE K Post-emergence action Damage to crop Herbicidal efficacy Dosageplants against Compound [g/ha] ZEAMX AVEFA LOLMU

80 50% 90% 90%

80 70% 70% 70%

The results of these exploratory comparative experiments show that thecompounds according to the invention having a thioamide structur havehigher herbicidal activity and cause less damage to crop plants than thestructurally closest compounds, known from WO 2012/028579 A1, having anamide structure.

1. An N-(tetrazol-5-yl)- or N-(triazol-5-yl)arylcarboxylic acidthioamide of formula (I) and/or a salt thereof

in which A represents N or CY, B represents N or CH, X represents nitro,halogen, cyano, formyl, thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,halo-(C₃-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,COR¹, COOR¹, OCOOR¹, NR¹COOR¹, C(O)N(R¹)₂, NR¹C(O)N(R¹)₂, OC(O)N(R¹)₂,C(O)NR¹OR¹, OR¹, OCOR¹, OSO₂R², S(O)_(n)R², SO₂OR¹, SO₂N(R¹)₂, NR₁SO₂R²,NR¹COR¹, (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹,(C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-CO₂R¹,(C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂,(C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R², NR₁R₂, P(O)(OR⁵)₂,CH₂P(O)(OR⁵)₂, (C₁-C₆)-alkylheteroaryl or (C₁-C₆)-alkylheterocyclyl,where the two last-mentioned radicals are each substituted by s radicalsfrom the group consisting of halogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy and halo-(C₁-C₆)-alkoxy, andwhere heterocyclyl carries n oxo groups, Y represents hydrogen, nitro,halogen, cyano, thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,halo-(C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl,halo-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, COR¹, COOR¹, OCOOR¹, NR¹COOR¹,C(O)N(R¹)₂, NR¹C(O)N(R¹)₂, OC(O)N(R¹)₂, CO(NOR¹)R¹, CHNOR¹, CH₂ONC(R³)₂,NR¹SO₂R², NR¹COR¹, OR¹, OSO₂R², S(O)_(n)R², SO₂OR¹, SO₂N(R¹)₂(C₁-C₆)-alkyl-S(O)_(n)R², NS(O)R⁶R⁷, S(O)R⁸NR⁹, (C₁-C₆)-alkyl-OR¹,(C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-CO₂R¹,(C₁-C₆)-alkyl-CN, (C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂,(C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R²,N(R¹)₂, P(O)(OR⁵)₂, CH₂P(O)(OR⁵)₂, (C₁-C₆)-alkylphenyl,(C₁-C₆)-alkylheteroaryl, (C₁-C₆)-alkylheterocyclyl, phenyl, heteroarylor heterocyclyl, where the six last-mentioned radicals are eachsubstituted by s radicals from the group consisting of halogen, nitro,cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy,(C₁-C₆)-alkoxy-(C₁-C₄)-alkyl and cyanomethyl, and where heterocyclylcarries n oxo groups, Z represents halogen, cyano, nitro, thiocyanato,halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl,halo-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, COR¹, COOR¹, OCOOR¹, NR¹COOR¹,C(O)N(R¹)₂, NR¹C(O)N(R¹)₂, OC(O)N(R¹)₂, C(O)NR¹OR¹, OSO₂R², S(O)_(n)R²,SO₂OR¹, SO₂N(R¹)₂, NR¹SO₂R², NR¹COR¹, (C₁-C₆)-alkyl-S(O)_(n)R²,(C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-OSO₂R²,(C₁-C₆)-alkyl-CO₂R¹, (C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂,(C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R²,N(R¹)₂, P(O)(OR⁵)₂, heteroaryl, heterocyclyl or phenyl, where the threelast-mentioned radicals are each substituted by s radicals from thegroup consisting of halogen, nitro, cyano, (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, S(O)_(n)—(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy and halo-(C₁-C₆)-alkoxy, and where heterocyclyl carries noxo groups, or Z may also represent hydrogen, (C₁-C₆)-alkyl or(C₁-C₆)-alkoxy if Y represents the S(O)_(n)R² radical, W representshydrogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl,(C₃-C₇)-cycloalkyl, (C₃-C₇)-halocycloalkyl, (C₁-C₆)-alkoxy,(C₁-C₆)-haloalkoxy, S(O)_(n)—(C₁-C₆)-alkyl, S(O)_(n)—(C₁-C₆)-haloalkyl,(C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₄)-haloalkyl, halogen,nitro, NR³COR³ or cyano, R represents (C₁-C₈)-alkyl, halo-(C₁-C₈)-alkyl,(C₂-C₈)-alkenyl, halo-(C₂-C₈)-alkenyl, (C₂-C₈)-alkynyl orhalo-(C₂-C₈)-alkynyl, where these six abovementioned radicals are eachsubstituted by s radicals from the group consisting of hydroxy, nitro,cyano, SiR⁵ ₃, PO(OR⁵)₂, S(O)_(n)—(C₁-C₆)-alkyl,S(O)_(n)—(C₁-C₆)-haloalkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy, N(R³)₂,COR³, COOR³, OCOR³, NR³COR³, NR³SO₂R⁴,O(C₁-C₂)-alkyl-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl, heteroaryl,heterocyclyl, phenyl, Q-heteroaryl, Q-heterocyclyl, Q-phenyl andQ-benzyl, where the seven last-mentioned radicals are each substitutedby s radicals from the group consisting of methyl, ethyl, methoxy,trifluoromethyl, cyano and halogen, and where heterocyclyl carries n oxogroups, or R represents (C₃-C₇)-cycloalkyl, heteroaryl, heterocyclyl orphenyl, each of which is substituted by s radicals from the groupconsisting of halogen, nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy,halo-(C₁-C₆)-alkoxy and (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, where heterocyclylcarries n oxo groups, Q represents O, S or NR³, R¹ represents hydrogen,(C₁-C₆)-alkyl, (C₁-C₆)-halo alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl,(C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl, (C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkenyl, (C₃-C₆)-halocycloalkyl,(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, (C₃-C₆)-cyclo alkyl-(C₁-C₆)-alkyl,phenyl, phenyl-(C₁-C₆)-alkyl, heteroaryl, (C₁-C₆)-alkylheteroaryl,heterocycl, (C₁-C₆)-alkylheterocycl, (C₁-C₆)-alkyl-O-hetero aryl,(C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR³-heteroaryl or(C₁-C₆)-alkyl-NR³-heterocyclyl, where the 21 last-mentioned radicals areeach substituted by s radicals from the group consisting of cyano,halogen, nitro, thiocyanato, OR³, S(O)R⁴, N(R³)₂, NR³OR³, COR³, OCOR³,SCOR⁴, NR³COR³, NR³SO₂R⁴, CO₂R³, COSR⁴, CON(R³)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl carries noxo groups, R² represents (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl,(C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl,(C₂-C₆)-haloalkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl,(C₃-C₆)-halocycloalkyl, (C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl, phenyl-(C₁-C₆)-alkyl,heteroaryl, (C₁-C₆)-alkylheteroaryl, heterocyclyl,(C₁-C₆)-alkylheterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,(C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR³-heteroaryl or(C₁-C₆)-alkyl-NR³-heterocyclyl, where the 21 last-mentioned radicals areeach substituted by s radicals from the group consisting of cyano,halogen, nitro, thiocyanato, OR³, S(O)R⁴, N(R³)₂, NR³OR³, COR⁵, OCOR³,SCOR⁴, NR³COR³, NR³SO₂R⁴, CO₂R³, COSR⁴, CON(R³)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl carries noxo groups, R³ represents hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl orphenyl, R⁴ represents (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl or phenyl, R⁵represents (C₁-C₄)-alkyl, R⁶ and R⁷ each independently of one anotherrepresent (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₃-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, halo-(C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, phenyl,heteroaryl or heterocyclyl, where the three last-mentioned radicals areeach substituted by s radicals from the group consisting of nitro,halogen, cyano, thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, R¹O(O)C, (R¹)₂N(O)C, R¹O, (R¹)₂N, R²(O)_(n)S,R¹O(O)₂S, (R¹)₂N(O)₂S and R¹O—(C₁-C₆)-alkyl, and where heterocyclylcarries n oxo groups, or R⁶ and R⁷ together with the sulfur atom towhich they are bonded form a 3- to 8-membered unsaturated, semisaturatedor saturated ring which contains, apart from the carbon atoms and apartfrom the sulfur atom of the sulfoximino group, in each case m ringmembers from the group consisting of N(R¹), O and S(O)_(n), and wherethis ring in each case is substituted by s radicals from the groupconsisting of nitro, halogen, cyano, thiocyanato, (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, R¹O(O)C, (R¹)₂N(O)C, R¹O,(R¹)₂N, R²(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S and R¹O—(C₁-C₆)-alkyl, andwhere this ring bears n oxo groups, R⁸ represents (C₁-C₆)-alkyl,(C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl, each of which is substituted by sradicals from the group consisting of nitro, halogen, cyano,thiocyanato, (C₃-C₆)-cycloalkyl, R¹(O)C, R¹(R¹ON═)C, R¹O(O)C,(R¹)₂N(O)C, R¹(R¹O)N(O)C, R²(O)₂S(R¹)N(O)C, R¹O(O)₂S(R¹)N(O)C,(R¹)₂N(O)₂S(R¹)N(O)C, R¹S(O)C, R¹O, R¹(O)CO, R²(O)₂SO, R²O(O)CO,(R¹)₂N(O)CO, (R¹)₂N, R¹O(R¹)N, R¹(O)C(R¹)N, R²(O)₂S(R¹)N, R²O(O)C(R¹)N,(R¹)₂N(O)C(R¹)N, R¹O(O)₂S(R¹)N, (R¹)₂N(O)₂S(R¹)N, R²(O)_(n)S, R¹C(O)S,R¹O(O)₂S, (R¹)₂N(O)₂S, R¹(O)C(R¹)N(O)₂S, R²O(O)C(R¹)N(O)₂S,(R¹)₂N(O)C(R¹)N(O)₂S and (R⁵O)₂(O)P, or (C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkenyl, phenyl, phenyl-(C₁-C₆)-alkyl, heteroaryl,heteroaryl-(C₁-C₆)-alkyl, heterocyclyl, heterocyclyl-(C₁-C₆)-alkyl,phenyl-O—(C₁-C₆)-alkyl, heteroaryl-O—(C₁-C₆)-alkyl,heterocyclyl-O—(C₁-C₆)-alkyl, phenyl-N(R¹)—(C₁-C₆)-alkyl,heteroaryl-N(R¹)—(C₁-C₆)-alkyl, heterocyclyl-N(R¹)—(C₁-C₆)-alkyl,phenyl-S(O)_(n)—(C₁-C₆)-alkyl, heteroaryl-S(O)_(n)—(C₁-C₆)-alkyl orheterocyclyl-S(O)_(n)—(C₁-C₆)-alkyl, each of which is substituted in thecyclic moiety by s radicals from the group consisting of nitro, halogen,cyano, thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, R¹(O)C, R¹(R¹ON═)C, R¹O(O)C, (R¹)₂N(O)C,R¹(R¹O)N(O)C, R²(O)₂S(R¹)N(O)C, R¹O(O)₂S(R¹)N(O)C, (R¹)₂N(O)₂S(R¹)N(O)C,R¹S(O)C, R¹O, R¹(O)CO, R²(O)₂SO, R²O(O)CO, (R¹)₂N(O)CO, (R¹)₂N,R¹O(R¹)N, R¹(O)C(R¹)N, R²(O)₂S(R¹)N, R²O(O)C(R¹)N, (R¹)₂N(O)C(R¹)N,R¹O(O)₂S(R¹)N, (R¹)₂N(O)₂S(R¹)N, R²(O)_(n)S, R¹C(O)S, R¹O(O)₂S,(R¹)₂N(O)₂S, R¹(O)C(R¹)N(O)₂S, R²O(O)C(R¹)N(O)₂S, (R¹)₂N(O)C(R¹)N(O)₂S,(R⁵O)₂(O)P and R¹O—(C₁-C₆)-alkyl, and where heterocyclyl carries n oxogroups, R⁹ represents hydrogen, nitro, halogen, cyano, (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, (C₃-C₆)-alkenyl, halo-(C₃-C₆)-alkenyl,(C₂-C₆)-alkynyl, halo-(C₃-C₆)-alkynyl, (C₃-C₆)-Cycloalkyl,halo-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, R¹(O)C, R²O(O)C, (R¹)₂N(O)C,R²S(O)C, (R¹)₂N(S)C, R¹(R¹O)N(O)C, R²(O)₂S(R¹)N(O)C,(R¹)₂N(O)₂S(R¹)N(O)C, R¹O, (R¹)₂N, R²(O)_(n)S,(R²)₃Si—(C₁-C₆)-alkyl-(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S, R¹(O)C(R¹)N(O)₂S,R²O(O)C(R¹)N(O)₂S, (R¹)₂N(O)C(R¹)N(O)₂S, R²(O)₂S(R¹)N(O)₂S, (R⁵O)₂(O)P,(R²)₃Si, R¹(O)C—(C₁-C₆)-alkyl, R¹O(O)C—(C₁-C₆)-alkyl,(R¹)₂N(O)C—(C₁-C₆)-alkyl, (R¹O)(R¹)N(O)C—(C₁-C₆)-alkyl,R²(O)₂S(R¹)N(O)C—(C₁-C₆)-alkyl, R¹O(O)₂S(R¹)N(O)C—(C₁-C₆)-alkyl,(R¹)₂N(O)₂S(R¹)N(O)C—(C₁-C₆)-alkyl, R¹O—(C₁-C₆)-alkyl,R¹(O)CO—(C₁-C₆)-alkyl, R²(O)₂SO—(C₁-C₆)-alkyl, R²O(O)CO—(C₁-C₆)-alkyl,(R¹)₂N(O)CO—(C₁-C₆)-alkyl, (R¹)₂N—(C₁-C₆)-alkyl,R¹(O)C(R¹)N—(C₁-C₆)-alkyl, R²(O)₂S(R¹)N—(C₁-C₆)-alkyl,R²O(O)C(R¹)N—(C₁-C₆)-alkyl, (R¹)₂N(O)C(R¹)N—(C₁-C₆)-alkyl,R¹O(O)₂S(R¹)N—(C₁-C₆)-alkyl, (R¹)₂N(O)₂S(R¹)N—(C₁-C₆)-alkyl,R²(O)_(n)S—(C₁-C₆)-alkyl, R¹O(O)₂S—(C₁-C₆)-alkyl,(R¹)₂N(O)₂S—(C₁-C₆)-alkyl, R¹(O)C(R¹)N(O)₂S—(C₁-C₆)-alkyl,R²O(O)C(R¹)N(O)₂S—(C₁-C₆)-alkyl, (R¹)₂N(O)C(R¹)N(O)₂S—(C₁-C₆)-alkyl,(R⁵O)₂(O)P—(C₁-C₆)-alkyl, (R²)₃Si—(C₁-C₆)-alkyl, or phenyl, heteroaryl,heterocyclyl, phenyl-(C₁-C₆)-alkyl, heteroaryl-(C₁-C₆)-alkyl orheterocyclyl-(C₁-C₆)-alkyl, each of which is substituted in the cyclicmoiety by s radicals from the group consisting of nitro, halogen, cyano,thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,R¹O(O)C, (R¹)₂N(O)C, R¹O, (R¹)₂N, R²(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S andR¹O—(C₁-C₆)-alkyl, and where heterocyclyl carries n oxo groups, mrepresents 0, 1, 2, 3 or 4, n represents 0, 1 or 2, s represents 0, 1, 2or
 3. 2. The N-(tetrazol-5-yl)- or N-(triazol-5-yl)arylcarboxylic acidthioamide and/or salt as claimed in claim 1 in which A represents N orCY, B represents N or CH, X represents nitro, halogen, cyano,thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₃-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, COR¹, OR¹, OCOR¹, OSO₂R²,S(O)_(n)R², SO₂OR¹, SO₂N(R¹)₂, NR¹SO₂R², NR¹COR¹,(C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-OCOR¹,(C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-CO₂R¹, (C₁-C₆)-alkyl-SO₂OR¹,(C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹or (C₁-C₆)-alkyl-NR¹SO₂R², (C₁-C₆)-alkyl-heteroaryl or(C₁-C₆)-alkyl-heterocyclyl, where the two last-mentioned radicals areeach substituted by s radicals from the group consisting of halogen,(C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, S(O)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxyand halo-(C₁-C₆)-alkoxy, and where heterocyclyl carries n oxo groups, Yrepresents hydrogen, nitro, halogen, cyano, thiocyanato, (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, halo-(C₃-C₆)-alkynyl, (C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkenyl, halo-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,COR¹, OR¹, COOR¹, CHNOR¹, CH₂ONC(R³)₂, OSO₂R², S(O)_(n)R², SO₂OR¹,SO₂N(R¹)₂, NS(O)R⁶R⁷, S(O)R⁸NR⁹, N(R¹)₂, NR¹SO₂R², NR¹COR¹,(C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-OCOR¹,(C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-CO₂R¹, (C₁-C₆)-alkyl-SO₂OR¹,(C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹,(C₁-C₆)-alkyl-NR¹SO₂R², (C₁-C₆)-alkyl-phenyl, (C₁-C₆)-alkyl-heteroaryl,(C₁-C₆)-alkyl-heterocyclyl, phenyl, heteroaryl or heterocyclyl, wherethe six last-mentioned radicals are each substituted by s radicals fromthe group consisting of halogen, nitro, cyano, (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, S(O)_(n)—(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy, (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl andcyanomethyl, and where heterocyclyl carries n oxo groups, Z representshalogen, cyano, nitro, thiocyanato, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₃-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,COR¹, COOR¹, C(O)N(R¹)₂, C(O)NR¹OR¹, OSO₂R², S(O)_(n)R², SO₂OR¹,SO₂N(R¹)₂, NR¹SO₂R², NR¹COR¹, (C₁-C₆)-alkyl-S(O)_(n)R²,(C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-OCOR¹, (C₁-C₆)-alkyl-OSO₂R²,(C₁-C₆)-alkyl-CO₂R¹, (C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂,(C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R²or 1,2,4-triazol-1-yl, or Z may also represent hydrogen, (C₁-C₆)-alkylor (C₁-C₆)-alkoxy if Y represents the S(O)_(n)R² radical, W representshydrogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy,(C₁-C₆)-haloalkoxy, S(O)_(n)—(C₁-C₆)-alkyl, S(O)—(C₁-C₆)-haloalkyl,(C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, halogen, nitro or cyano, R represents(C₁-C₈)-alkyl, halo-(C₁-C₈)-alkyl, (C₂-C₈)-alkenyl,halo-(C₂-C₈)-alkenyl, (C₂-C₈)-alkynyl, halo-(C₂-C₈)-alkynyl, where thesesix abovementioned radicals are each substituted by s radicals from thegroup consisting of nitro, cyano, SiR⁵ ₃, P(OR⁵)₃,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy, N(R³)₂,COR³, COOR³, OCOR³, NR³COR³, NR³SO₂R⁴, (C₃-C₆)-cycloalkyl, heteroaryl,heterocyclyl, phenyl, Q-heteroaryl, Q-heterocyclyl, Q-phenyl andQ-benzyl, where the seven last-mentioned radicals are each substitutedby s radicals from the group consisting of methyl, ethyl, methoxy,trifluoromethyl, cyano and halogen, and where heterocyclyl carries n oxogroups, or R represents (C₃-C₇)-cycloalkyl, heteroaryl, heterocyclyl orphenyl, each of which is substituted by s radicals from the groupconsisting of halogen, nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy,halo-(C₁-C₆)-alkoxy and (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, Q represents O, Sor NR³, R¹ represents hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, phenyl, phenyl-(C₁-C₆)-alkyl, heteroaryl,(C₁-C₆)-alkylheteroaryl, heterocyclyl, (C₁-C₆)-alkylheterocyclyl,(C₁-C₆)-alkyl-O-heteroaryl, (C₁-C₆)-alkyl-O-heterocyclyl,(C₁-C₆)-alkyl-NR³-heteroaryl or (C₁-C₆)-alkyl-NR³-heterocyclyl, wherethe sixteen last-mentioned radicals are each substituted by s radicalsfrom the group consisting of cyano, halogen, nitro, OR³, S(O)_(n)R⁴,N(R³)₂, NR³OR³, COR³, OCOR³, NR³COR³, NR³SO₂R⁴, CO₂R³, CON(R³)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl carries noxo groups, R² represents (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, phenyl, phenyl-(C₁-C₆)-alkyl, heteroaryl,(C₁-C₆)-alkylheteroaryl, heterocyclyl, (C₁-C₆)-alkylheterocyclyl,(C₁-C₆)-alkyl-O-heteroaryl, (C₁-C₆)-alkyl-O-heterocyclyl,(C₁-C₆)-alkyl-NR³-heteroaryl or (C₁-C₆)-alkyl-NR³-heterocyclyl, wherethese sixteen last-mentioned radicals are each substituted by s radicalsfrom the group consisting of cyano, halogen, nitro, OR³, S(O)_(n)R⁴,N(R³)₂, NR³OR³, NR³SO₂R⁴, COR³, OCOR³, NR³COR³, CO₂R³, CON(R³)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl carries noxo groups, R³ represents hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl or (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,R⁴ represents (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl, R⁵represents methyl or ethyl, R⁶ and R⁷ each independently of one anotherrepresent (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,halo-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl,halo-(C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, phenyl, heteroaryl or heterocyclyl,where the three last-mentioned radicals are each substituted by sradicals from the group consisting of nitro, halogen, (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, R¹O(O)C, (R¹)₂N(O)C, R¹O, (R¹)₂N, R²(O)_(n)S andR¹O—(C₁-C₆)-alkyl, and where heterocyclyl carries n oxo groups, or R⁶and R⁷ together with the sulfur atom to which they are attached form a3- to 8-membered unsaturated, partially saturated or saturated ringwhich contains, in addition to the carbon atoms and in addition to thesulfur atom of the sulfoximino group, in each case m ring members fromthe group consisting of N(R¹), O and S(O)_(n), and where this ring is ineach case substituted by s radicals from the group consisting ofhalogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, R¹O(O)C, (R¹)₂N(O)C, R¹O,(R¹)₂N, R²(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S and R¹O—(C₁-C₆)-alkyl, andwhere this ring carries n oxo groups, R⁸ represents (C₁-C₆)-alkyl whichis in each case substituted by s radicals from the group consisting ofhalogen, cyano, (C₃-C₆)-cycloalkyl, R¹(O)C, R¹(R¹ON═)C, R¹O(O)C,(R¹)₂N(O)C, R²(O)₂S(R¹)N(O)C, R¹O, (R¹)₂N, R¹(O)C(R¹)N, R²(O)₂S(R¹)N,R²O(O)C(R¹)N, (R¹)₂N(O)C(R¹)N, R²(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S,R¹(O)C(R¹)N(O)₂S, R²O(O)C(R¹)N(O)₂S and (R¹)₂N(O)C(R¹)N(O)₂S or(C₃-C₆)-cycloalkyl which is in each case substituted by s radicals fromthe group consisting of halogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, R¹O(O)C and (R¹)₂N(O)C, R⁹ represents hydrogen,nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,halo-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, R¹(O)C, R²O(O)C, (R¹)₂N(O)C,R²(O)₂S, R¹(O)C—(C₁-C₆)-alkyl, R¹O(O)C—(C₁-C₆)-alkyl,(R¹)₂N(O)C—(C₁-C₆)-alkyl, R¹O—(C₁-C₆)-alkyl, (R¹)₂N—(C₁-C₆)-alkyl orR²(O)_(n)S—(C₁-C₆)-alkyl, m represents 0, 1 or 2, n represents 0, 1 or2, s represents 0, 1, 2 or
 3. 3. The N-(tetrazol-5-yl)- orN-(triazol-5-yl)arylcarboxylic acid thioamide and/or salt as claimed inclaim 1 in which A represents N or CY, B represents N or CH, Xrepresents nitro, halogen, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, OR¹, S(O)_(n)R², (C₁-C₆)-alkyl-S(O)_(n)R²,(C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂,(C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R², (C₁-C₆)-alkylheteroarylor (C₁-C₆)-alkylheterocyclyl, where the two last-mentioned radicals areeach substituted by s halogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy and halo-(C₁-C₆)-alkoxy radicals,and where heterocyclyl carries n oxo groups, Y hydrogen, nitro, halogen,cyano, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, OR¹, S(O)R², SO₂N(R¹)₂,NS(O)R⁶R⁷, S(O)R⁸NR⁹, N(R¹)₂, CHNOR¹, CH₂ONC(R³)₂, NR¹SO₂R², NR¹COR¹,(C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-CON(R¹)₂,(C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R²,(C₁-C₆)-alkyl-phenyl, (C₁-C₆)-alkyl-heteroaryl,(C₁-C₆)-alkyl-heterocyclyl, phenyl, heteroaryl or heterocyclyl, wherethe six last-mentioned radicals are each substituted by s radicals fromthe group consisting of halogen, nitro, cyano, (C₁-C₆)-alkyl,halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, S(O)_(n)—(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy, (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl andcyanomethyl, and where heterocyclyl carries n oxo groups, Z representshalogen, cyano, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, S(O)R²,1,2,4-triazol-1-yl, or Z may also represent hydrogen, methyl, methoxy orethoxy if Y represents the S(O)_(n)R² radical, W represents hydrogen,methyl, ethyl, methoxymethyl, methoxy, fluorine, chlorine orS(O)_(n)CH₃, R represents (C₁-C₈)-alkyl, halo-(C₁-C₈)-alkyl,(C₂-C₈)-alkenyl, halo-(C₂-C₈)-alkenyl, (C₂-C₈)-alkynyl,halo-(C₂-C₈)-alkynyl, where these six abovementioned radicals are eachsubstituted by s radicals from the group consisting of cyano,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy, COR³,COOR³, OCOR³, NR³COR³, NR³SO₂R⁴, (C₃-C₆)-cycloalkyl, heteroaryl,heterocyclyl and phenyl, where the three last-mentioned radicals areeach substituted by s radicals from the group consisting of methyl,ethyl, methoxy, trifluoromethyl, cyano and halogen, and whereheterocyclyl carries 0 to 2 oxo groups, or R represents phenyl which issubstituted by s radicals from the group consisting of halogen, nitro,cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy and(C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, R¹ represents hydrogen, (C₁-C₆)-alkyl,(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cyclo alkyl,(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, phenyl,phenyl-(C₁-C₆)-alkyl, heteroaryl, (C₁-C₆)-alkylheteroaryl, heterocyclyl,(C₁-C₆)-alkylheterocyclyl, (C₁-C₆)-alkyl-O-hetero aryl,(C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR³-heteroaryl or(C₁-C₆)-alkyl-NR³-heterocyclyl, where the sixteen last-mentionedradicals are each substituted by s radicals from the group consisting ofcyano, halogen, nitro, OR³, S(O)R⁴, N(R³)₂, NR³OR³, COR³, OCOR³,NR³COR³, NR³SO₂R⁴, CO₂R³, CON(R³)₂ and(C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl carries noxo groups, R² represents (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl or(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, each substituted by s radicals fromthe group consisting of halogen and OR³, R³ represents hydrogen or(C₁-C₆)-alkyl, R⁴ represents (C₁-C₆)-alkyl, R⁶ and R⁷ independently ofone another each represent methyl, ethyl or n-propyl, or R⁶ and R⁷together with the sulfur atom to which they are attached form a 5- or6-membered saturated ring which, in addition to the carbon atoms and inaddition to the sulfur atom of the sulfoximino group, contains m oxygenatoms, R⁸ represents methyl, ethyl or n-propyl, R⁹ represents hydrogenor cyano, m represents 0 or 1, n represents 0, 1 or 2, s represents 0,1, 2 or
 3. 4. A herbicidal composition which comprises a herbicidallyeffective amount of at least one compound of formula (I) and/or salt asclaimed in claim
 1. 5. The herbicidal composition as claimed in claim 4in a mixture with one or more formulation auxiliaries.
 6. The herbicidalcomposition as claimed in claim 4, comprising at least one furtherpesticidally active substance selected from the group consisting ofinsecticides, acaricides, herbicides, fungicides, safeners and growthregulators.
 7. The herbicidal composition as claimed in claim 6,comprising a safener.
 8. The herbicidal composition as claimed in claim7, comprising cyprosulfamide, cloquintocet-mexyl, mefenpyr-diethyl orisoxadifen-ethyl.
 9. The herbicidal composition as claimed in claim 6,comprising a further herbicide.
 10. A method for controlling one or moreunwanted plants, comprising applying an effective amount of at least onecompound of formula (I) and/or salt as claimed in claim 1 to a plantand/or to a site of unwanted vegetation.
 11. A compound of formula (I)and/or salt as claimed in claim 1 capable of being used for controllingan unwanted plant.
 12. The compound and/or salt as claimed in claim 11,capable of being used for controlling one or more unwanted plants in oneor more crops of one or more useful plants.
 13. The compound and/or saltas claimed in claim 12, wherein the useful plants are transgenic usefulplants.